BoS USA 2023 – The Sigmacorn Notes

Notes from the Sigmacorns at BoS USA 2023.

As usual, you really had to be there but here are the Sigmacorn notes…

9:00 Mark Littlewood: Opening remarks

  • Welcome to BoS!
  • Attendee hub can be accessed via QR code on your nametag
  • Code of conduct is available here
  • Members of the team are wearing gray shirts
  • Mayor Baldwin is unfortunately stuck in traffic, but Mark is more excited to meet her
  • Mayor Baldwin will be presenting after the first speaker
  • BoS is in Raleigh to stay: easier trip through immigration, bluegrass festivals, and football!

9:15 Jason Cohen: Building your Permanent Defensible Strategy

Slides from Jason Cohen’s Talk

  • A glass of water at room temperature has 7 septillion molecules
  • Each molecule is moving at twice the speed of sound
  • If aligned, the water would shoot off at that speed (like a watersaw)
  • In tech support, most tickets are produced by small clients, but some are generated by very large clients (which you want to keep)
  • Main problem: how do you get people aligned on their goals? How will we win?
  • When everyone is doing (in their opinion) the right thing in the moment, the performance at a high level is subpar
  • A great strategy that we’re not good at executing is a bad strategy
  • Finding the problem: reverse-engineering the status quo as an “alien” — someone who cannot impart any judgment in the company
  • Often, these values and strategies are not present in academic settings
  • Questions to ask
  • What are people thinking right now? What are people doing right now?
  • What is it that this company is doing?
  • Why these questions should be asked
  • Feedback, performance, and competitor relations
  • Feelings (pride or jealousy) about own company and others
  • Relevance of important values and aspirations
  • Exact choices: Extract the choices that your company makes as attributes
  • What does the company do?
  • For example: a statement such as “Our company makes a cheap product with few features and great support”
  • Pair with opposites and identify choices that companies make
  • Act like a lawyer: make a great case for the opposition
  • Extract choices: refine these choices into intelligent decisions that could have been made
  • Identify attributes — there are no strengths or weaknesses, but they are completely contextual and have varying consequences
  • Something we can take advantage of/deal with
  • Decisions without reasonable alternatives don’t count as decisions — the choice is trivial
  • Break down choices into things that can be decided
  • Consistent choices: identify conflicts
  • Not all decisions make sense in context, and context about consequences need to be identified
  • Consequences and opportunities in multiple choices may conflict
  • This can be mitigated by identifying consistent archetypes: alternative product strategy can resolve idea conflicts
  • Choosing to prioritize actions which change the significance of consequences and opportunities changes and works around them
  • Reframe these strategies as a consistent framework; make it work
  • These actions build up a set of decisions (consistencies and changes) which align
  • Water molecules in a glass of water
  • Decision circles: a visual representation of the decisions which are made
  • Separate out decisions which are changes and decisions which maintain the status quo
  • Some sets of decisions reinforce each other (green line)
  • others contradict (red line)
  • And others do not interact (no line)
  • Some choices specifically serve to address a conflict between two choices
  • The decision circle can be redrawn to identify conflicts and strategic pillars
  • Groups of choices which either generally supplement each other or generally conflict against another can identify ideal changes
  • Strategy
  • Pivots: changes in choices that are not trivial
  • Highlight changes which are extra hard (like changes in philosophy and identity)
  • For example: design
  • Things which aren’t effectively leveraged should be identified too
  • Competitive differentiation
  • Competition cannot be ignored
  • Customers look at competitors, and strategy must take competition into account
  • Competition can be analyzed based on their behavior, in the same way that one would look at yourself
  • Competitors’ good decisions can be taken and applied in the context of own company
  • Some decisions are special and some are commodity in the context of the market
  • Some factors are significantly important (voters), and decide whether or not you or your competitor “win” the customer
  • A pivot can lead to voters as well as a unique distinction in the market
  • External constraints
  • Secular trends and industry trends guide strategic progression
  • Choosing to pursue trends can yield consequential or opportunistic outcomes
  • For example: pursuing an AI-forward strategy
  • Strengths: jump on now or else you’ll be behind
  • Weaknesses: it could be useless and take resources from other aspects
  • Companies are switching softwares just because of design
  • People start using them, which forces companies to adopt (e.g. Linear for project management)
  • Decisions made on trend may be conjoined in contextual groups, similar to pillars
  • Segmenting market to reach “best of both worlds”
  • For example: Red Hat (RHEL), mongoDB, elastic, Slack
  • Enterprise vs core technology mass-market consumer product
  • Choices can be taken to extreme levels to distinguish a small company in a competitive market
  • Case study: Southwest Airlines
  • Aspects which are inherently bad for certain customer experiences
  • Being strong about extreme choices and accepting decisions with bad consequences lead to extreme choices with opportunities
  • Results in SWA being the only profitable airline in 1996 & being never bankrupt
  • Companies may refuse to adopt an extreme model which gives them a competitive advantage
  • They can choose to adopt aspects of a functional model, but the entire network is what gives a competitive advantage to companies with an extreme approach
  • Case study: craigslist
  • Confidently adopting strong corporate and product principles
  • Durable: strong in the face of specialist apps (most of which did not make it)
  • End goal for any self-started/self funded company from a series of decisions is to create a Moat: permanent competitive advantage
  • Network effect
  • Facebook, eBay
  • Unique, secret intellectual property
  •  Coca Cola formula, Google search algorithm
  • System of record
  • Salesforce, Workday
  • Mach 2 strategy
  • Southwest, Craigslist
  • Mutually-reinforcing extreme decisions can put a moat in place
  • In the end, all decisions should be made reflecting the overall strategy

10:15 Mayor Mary-Ann Baldwin: Welcome to Raleigh

  • Welcome to Raleigh!
  • Special thanks to SafraSofTech and Atomic Abject for opening business here
  • 12 years ago, started InnovateRaleigh
  • Catalyst for innovation and entrepreneurship
  • Didn’t know that there was an entrepreneur community until first innovators’ summit
  • Lots of people showed up!
  • Raleigh is in the top 5 for entrepreneurial activity
  • Asked to participate for Over the Edge for Special Olympics harnessed in and rappel off of a 30-story building
  • Gabi (person with down syndrome) started a non-profit which employs people who live with disabilities (people with special powers!)
  • The struggles she faces each day inspires Mayor Baldwin to take on this challenge
  • Police chief agreed to do this with Mayor Baldwin
  • Having someone trustworthy was integral
  • Having encourage from the chief was also critical
  • Lessons to be learned
  • You have to challenge yourself: the status quo does not get you anywhere
  • Challenges help address bigger needs
  • Take that risk: it’s terrifying, empowering — just like running a business
  • Surround yourself with people you trust
  • People who are honest and encouraging: your support system
  • Have a trusted advisor
  • Choose to do things to make an impact, not because of ego
  • Have a great time in Raleigh!

10:45: Randeep Sidhu: Life and Death Decisions

  • Insight into the world of a CPO of rapid technology development company in UK
  • Importance of a clear conscience
  • Products and decisions impact users — in healthcare, this is life and death for clients
  • 4 lessons during stress
  1. My behavior
  2. Teams’ behavior
  3. Users’ behavior
  4. Why impact is hard
  • National Health Service built a COVID-19 tracking app, which failed
  • Identified high risk communities: socioeconomically disadvantaged, POC, etc.
  • Surveyed people to check what app would be actually useful
  • Departed Babylon to work for NHS in less than a week
  • UK Context: inappropriate to leave job in a week — NHS reached out to employer
  • End choice: to clear conscience, and out of confidence that better could be done
  • NHS app technical details
  • Used cross-platform API created by Apple, Google and implemented QR check in
  • Algorithms for exposure developed by Alan Turing Institute
  • Deadlines, challenges, and choices
  • Superhero mentality: to ship the app in 6 weeks, must be able to do job
  • Internationalization to 12 languages, serving >98% of language speakers
  • Debate around implementing in-app language selection
  • Research contradicted request
  • However, research sampled bad population: no people with English as second language
  • Team hated him afterwards
  • Did not understand situational power balance
  • Reality on the ground
  • Requirements: launch in 6 weeks, universal product, but no product team
  • Working with 80+ engineers, but no product team
  • Technology is not universal, but healthcare needs to be
  • Common themes at workplace
  • Repeating self
  • People assume the worst
  • Everything became “emergency”
  • Under stress, neither the team nor yourself are at their best
  • Adrenaline → ↑ anxiety, ↑ hypervigilance
  • Improvement through framework: Maslow’s hieararchy of needs
  • Prioritized application features on personal safety
  • Bottom level: Safety: Physical
  • Can you get the app?
  • Will getting the app be dangerous for you?
  • Will you be able to use it without data?
  • [rest of triangle from slides]
  • Allowed developers to understand priorities of application development
  • Focus on the bottom, more fundamental issues
  • Helped align focus on which parts needed to be built the most
  • Have to curate an environment where it is okay to fail
  • Laughter reduces adrenaline
  • Example of conflict and generation of issue within app
  • Content management system vs. hardcoding languages into the app
  • Poor internationalization of pages and videos
  • Nobody on the team has experience in the app
  • Soliciting language review from native speakers & being contacted by other countries and governmental entities regarding errors
  • Trust within the government
  • Users were stressed and were scared of the app
  • People hated it and wanted to keep hating it (confirmation bias) after launch
  • Motivating people cannot be done using more force or pressure
  • Cannot use threats or requirements to increase participation
  • Gave users a sense of control over their experience
  • Used the app to assure users with a sense of comfort
  • Ensured that the system as a whole was easy to use and private
  • Think about increasing number of users as an analogy to making a bullet go faster
  • Adding more gunpower is like threats and pressure, it will increase speed to some extent but the bullet will eventually explode
  • Making the bullet more aerodynamic decreases friction, increasing speed much better
  • Research regarding inequitable distribution of adoption
  • Established people within government alienated and singled out marginalized populations
  • Speaking up led to government employees turning against a contrasting opinion
  • Needed to research what people actually trusted — who/what each demographic trusted
  • Challenging the status quo led to this conflict
  • Two groups of people:
  • Those who are content with the society we live in today (superheroes)
  • Do not change the world
  • Only do things in response to something popular
  • Those who are not satisfied and want change (villains)
  • Upset the status quo
  • Challenges a preconceived notion
  • Creating change generally entails challenging the status quo
  • This creates discomfort, leading to people turning against you
  • Challenging the norm makes one seem like a villain
  • Poor methods turn one into a villain
  • Reality 1: With stress, you’re more likely to act as the villain, not the superhero
  • A righteous mission does not make you the hero
  • Reality 2: Control versus chaos
  • Reduce the unpredictability of the environment
  • Reality 3: Chaos versus control
  • Users need a sense of increased control & reduced friction
  • Reality 4: Changing the status quo will make you seem like a villain
  • You need to be aware of this and stay confident
  • Punch up not down

11:45: Suresh Menon: Dancing with Elephants

  • Hardware and software are inherently different: it is difficult to collaborate
  • Speaking with leaders yields varying results
  • Road trip analogy for strategies for innovation:
  • Software might experiment and prototype and immediately travel
  • Hardware might spend months meticulously planning out a trip
  • Software has to live with a degree of uncertainty
  • Well-run companies find it very difficult to innovate
  • Larger companies have a smaller tolerance for risk
  • These companies may not jump on monetizing opportunities
  • Great ideas tend to die
  • Larger companies may be “addicted” to acquisition
  • Weighing operational expenditures versus cash on hand
  • Can simply spend money to acquire business who have taken risk
  • 70-90% of acquisitions fail
  • Failure is defined as not meeting the goal which originally spurred the initiation of the acquisition
  • Why do large companies acquire?
  • Integrating platforms lead to opportunities and questions
  • Easier to integrate software into a workflow for the parent company
  • Raises questions about software capabilities and market performance
  • Purchasing companies to fill a competitive gap
  • Reacting to market trends to evaluate who is available and fills product niche
  • Driving growth in the market and expanding based on opportunities
  • Fulfilling a need in a particular space
  • Identifying smaller companies that address a broader scope
  • Vertical integration
  • Competitors can cause large disruptions by taking control over supply chains
  • Strategic benefit from acquiring a larger scope of production control
  • Market consolidation        
  • Owning more of the market to control more customers or revenue
  • Generally results in failures
  • What is the acquiring company looking at as they evaluate the company?
  • Growth acceleration: how to generate a higher lead in the market
  • Accessing a wider market
  • Directly accessing product and intellectual property
  • Diversify capabilities for corporate fit
  • Includes regulatory and geographic factors
  • When acquiring: is this a good enough match?
  • Changing financial composition for the company
  • A company may wish to change balance of profitability and assets
  • Why do acquisitions go through and become successful?
  • Software acquisitions aren’t made for monetary gain, but for retaining people
  • The most important gain is the acquisition of intellectual property through people
  • Keeping people along with software resources allows for growth
  • In most cases, the founders don’t stay around — they aren’t tied to the IP
  • Cultural fit prioritized in order to integrate into an acquiring company
  • Successfully translating cultures across company lines is important
  • Merging systems from acquired company into larger company
  • Difficult to conjoin two incompatible workflows
  • Ensure that all systems are accounted for
  • Founders having a growth path in the joined company
  • Key figures in the acquired company leave because they lose control
  • People who stay have a refined role in the new configuration
  • Variety of success and failure stories
  • Acquired companies can take parent company in a completely different direction
  • Acquired companies can become the most integral part (or even replace) parent
  • Try to understand how to maximize value given constraints
  • Why might other companies want to acquire you? What factors are required to succeed?
  • Seeing legacy grow and scaling up career paths for employees


  • How often do you see acquisitions on the basis of killing innovation?
  • Quite often — rarely seen in public companies, but private equity funds do this quite often
  • What resource would you recommend for founders that would help us be better prepared for acquisition?
  • A lot of the resources tell what did not work, not what did work
  • Recommendation: there is no straight formula. Have a trusted advisor who is being either on the acquiring side or the acquisition side who can guide you through the process
  • Need to understand: what is the acquiring side like? What would make it easiest to integrate the process into their business
  • Every segment is different — every acquiring company is different as to what they are looking for. It is important to have a kind of a trusted advisor
  • How would you position yourself best to make an acquisition most valuable?
  • Understand what the motivations are for acquiring a company
  • How do you rate the value of investment bankers in the process?
  • Treat them as a necessary evil and work your way around it. Know how to leverage them, but know how to work around them as well
  • Their motivations are different from either the company that wants to acquire you or you as one that is being acquired
  • Is enterprise value being considered in the rationale for acquiring a company?
  • Sometimes — competitive acquisitions is no different from buying a house. It comes down to how badly the acquiring company wants to have the business
  • It is down to the willingness of the acquiring company to have it
  • Very rarely is it down to capital allocation in software
  • How would you class the purchase by Adobe for Figma?
  • It looks like (based on the value of the company) that Figma was a significant threat to their company, and decided it was better to own the asset now
  • Perhaps it was not to kill innovation, but rather to get to a higher technical level quickly.
  • How badly does Adobe need that business?
  • In your 27 acquisitions, how many of you did you find to target and how many of those targeted to find you/ Could you speak to your experience finding
  • Role in finding acquisitions
  • There are very few software acquisitions led by anyone running the product business. Although, I think out of 27, there was 1 led by sales (it ended up failing)
  • There has to be a product sponsor which is going out and saying “I need this.” It’s almost always product led

14:15: SigmaCorns: A New Robot Generation

  • North Carolina School of Science and Mathematics: a public, residential STEM high school with two campuses in the state of North Carolina
  • FIRST® Robotics Competition connected Jacob and Ayush
  • OpenAI public demo of GPT-3 was eye-opening
  • Improvements upon GPT-2 meant that it could generate human-like text
  • Call to action: mentorship from Carl Ryden
  • FIRST Tech Challenge teams demand substantial resources in guidance
  • Saw use case of artificial intelligence to solve a gap in mentorship
  • Created FOSTER — FTC Optimized Sentiment and Text Engagement Robot
  • Founded LRNT to address broader educational initiatives
  • Niche was giving individualized learning approach to students with fewer resources
  • “Build Iron Man suits, not Terminators”
  • Suite of tools instead of fully autonomous platform
  • Augmented knowledge of skilled educators instead of replacing them
  • Extending this through trials w/UC Berkeley, Harvard researchers
  • Deploying model for data science at NCSSM
  • Luck – Look for bigger luck surface area
  • Connected with Plastic Labs; working on AI-assisted education
  • Their corporate focus was to augment talent, not to replace it
  • Their product — — offers personalized AI helper


  • How are you living in the future? What around you is missing in your day-to-day life?
  • Someone talked about how they ran their business — there are two CEOs: one CEO of today, and a CEO of the future
  • One CEO was responsible for keeping the train on the rails, which frees up the other person to think about what’s next
  • Every single startup is a constantly-moving train; eventually, the tracks will run out, and we will have to place the rails so that the train has a place to go
  • How are you living in the future? What around you is missing in your day-to-day life?
  • Always challenging the team to think bigger, and not being afraid to bring those ideas to the table. There are no crazy ideas; there are only ideas
  • We must talk about those ideas so that we can build that future
  • Guardrails on the AI — do you all put any safeguards in place to prevent students from just going straight to the answer?
  • For LRNT, the AI always knows the answer, but it is prompted to not just tell the student
  • It tries to identify what misunderstandings the student might have, and to fix it
  • Plastic Labs’ bloom uses theory of mind & socratic methods to address the problem
  • The AI is trained to help the student when they need help, prompting them to learn about where they need to go, but not giving them the answer
  • What are your thoughts on how we make AI a useful technology over “just another solution”?
  • All of the AI tools are distinct from other products in that they are a polished product with some tangible utility instead of being just “cool”
  • There are a bunch of chatbots that emulate the personality of celebrities as a novelty, but AI has practical uses in day-to-day operations

16:45: Bob Moesta: Jobs-to-be-Done in the Enterprise

  • Part 1: People don’t buy products; they hire them to make progress in their lives
  • People do not randomly switch between products
  • Finding technology-agnostic requirements from the customer
  • “What does the customer want, except they don’t tell us what they want?”
  • Infer practical methods from a customer’s current perspective to their wanted outcome
  • Circumstances (jobs) have to be identified
  • The struggling moment is the seed for all innovation
  • Why do they (customer) struggle?
  • “Questions create spaces in the brain for solutions to fall into”
  • Most customers do not know what is possible, but they do know what outcome they want
  • Extracting this is very important
  • Customers lie (but not necessarily maliciously)
  • There is a disconnect between what companies feel they sell and what consumers think they buy
  • Engineering a solution does not imply that demand will come: product-market disconnect
  • Disconnect between supply-side and demand-side opinions
  • Must understand the other side to face a problem effectively
  • The key to business is finding and understanding the struggling moment for consumers
  • Being knowledgeable about requirements and behavior helps product success
  • For example, Casper made mattresses easy to buy, not the superior product
  • To build a better product, it is necessary to get far away from the product
  • Distance yourself with the 5 why’s
  • Interacting and understanding people (the people who buy)
  • Four forces of progress
  • Fuel
  • Push of the situation: factors which do not have anything to do with the product which deter the consumer from adopting it
  • Pull of new situation: factors in a new situation which attract the consumer towards working to get to the new product
  • Friction
  • Habit of the present: nostalgia and emotional attachment to existing situation
  • Anxiety of the new solution: uncertain feeling about change
  • Progress made by people follows a specific timeline
  • Passive looking: people subconsciously identify a cool product after thinking about it
  • Active looking: window shopping — no idea of what they want yet
  • Deciding: customers have to make tradeoffs and choose which ones they take
  • 60% of B2B transactions lead to nothing as consumers aren’t assisted
  • Consumers do not pick a product; they eliminate to it
  • Consuming the product, and then being satisfied with it
  • Initial outcomes help consumers understand whether they are happy with the product
  • Social and emotional aspects impact consumer choices
  • Understanding how people make a tradeoff between these factors is critical
  • Case studies/use cases for jobs-to-be-done
  • Cafeteria
  • Interviewed a lot of people about breakfast
  • People wouldn’t get food if they couldn’t get it in 90 seconds
  • Changed food to be prepped faster and cafeteria got 4X more people
  • Intercom
  • As a product, bundles managing consumer data all together for a company
  • Billed individually and segmented on its own
  • Listening to feedback and research yielded patterns of platform requirements
  • Scaled product back down to the 4 essentials that customers were looking for
  • Each time they tried to push new platform to users it gave negative returns
  • Created huge growth
  • Human resources
  • Employees themselves hire companies to assist them in progressing their life
  • Interviewing those who switched jobs: each one assigned it to luck
  • A variety of factors push people away from a job: people will not look at other jobs unless there is something pushing them away from the job
  • More money is also more respect and more responsibility
  • Four patterns of changing jobs:
  1. Burnt out
  2. Overloaded
  3. Desire for more growth
  4. Feeling unappreciated
  • Lots of information is lost between the job description, résumé, and review
  • Change mindset from hiring to fill a position → hiring to help an employee progress
  • Russell: mapping employee progress and interest throughout career
  • Steps to apply jobs-to-be-done
  • Find struggling moments
  • Think progress, not products or service
  • Identify trade off — “what are you willing to give up”


  • What is the secret to making sure the customer knows the product is ready when you start looking?
  • The things that have to happen to them is how you know where to be and when to be
  • Ultimately, most of the people have had an awkward conversation about downsizing a house when one of their friends passed away — moved advertising for services to funeral homes from real estate
  • If you don’t have a product in market yet, and you have an idea about something, who do you interview if there’s nothing to hire?
  • If I build the product I want to build, what are people going to fire?
  • Understanding what people are going to fire so that a better product can be built
  • How do you, if you are not the first in charge, walk into a room with people in charge, say that you’re going to move all of the ads to the obituary?
  • Firstly: interview the executive and ask them about what they just bought; set up a test
  • Interview the executive in front of people who are familiar with the situation: makes it so that executive can understand the whole story
  • How do you bring a research background to business in a more accessible way that is not too lengthy but eliminates bias?
  • Interviews for HR study last an hour and are free flowing: treating each story as independent but then identifying each pattern
  • Causal mechanisms can be shown to the interviewee and they understand sets of things that happen which makes things want to change
  • On both sides of the “wall”, what typically causes a pivot?
  • The market itself can cause a pivot and where the struggling moments are
  • Also depends on where the technology lies
  • Functional, social, emotional. I remember there was a 4th one, financial
  • Financial one as functional: anything that is super rational falls into that functional bucket
  • Emotional is more like chemistry — positive and negative emotions which behave like electromagnetic fields which behaves differently than objective function

10-03 (Tuesday)

9:00: April Dunford: How Your Differentiated Value Should Drive Your Sales Pitch

  • Often times software companies call product walkthroughs → pitches
  • We often don’t want to seem like a used car salesman because we:
  • Don’t want to lie
  • Don’t want to be selfish and just want money
  • Differentiated value: what you can do for customers that no other company on the market can do, “why pick us”, being like a guide vs a used car salesman
  • Example of “misrepresenting it”
  • IBM
  • Sales people used “itibilities” (scalability, etc) and benchmarks which changed every week due to competitor
  • The major difference was the values, where IBM was more focused on innovation compared to ORACLE
  • Example of “stretching it”
  • Watcom SQL
  • Is “compatible” with other SQL’s through extensions, so compatible to some extent but not fully
  • Sales rep didn’t understand the tiny difference so they thought it was fully compatible
  • Example of “Not Getting to the Core of it”
  • LevelJump Solutions
  • Buried the most valuable feature under little valuable things
  • Getting to differentiated value
  • What alternatives to the product
  • Differentiated value
  • Product walkthroughs are all about the product which leaves the customer to connect the product to why they need it
  • Most buyers don’t know about the software they are buying
  • The buyer is generally worried when deciding to buy the product
  • Easiest decision is to do nothing
  • What should you do to help the buyer make choices?
  • Give perspectives on the market
  • Give pros and cons for the alternatives
  • Calm Confidence
  • Don’t sell to bad fits, fight for business in good fits
  • Sales pitch structure
  1. The setup
  1. Give market insight
  2. Explore alternatives
  3. Describe the perfect world
  4. Value
  5. How the product fulfills features of the perfect world


  • Significant percentage of millennials do not want to talk to sales representatives. With millennials starting to make all purchases, how do you address that?
  • Lots of companies don’t want to get involved with salespeople and ask their customers to figure it out, but with the pandemic it has been making a comeback.
  • When you don’t need a sales representative to make decisions it’s alright not to have a sales representative, but as you go up the market you are going to need someone to guide you. A large percentage of job descriptions involve making purchasing decisions.
  • I don’t think sales will be going away in the next 10 years, it may change but it won’t disappear.
  • How do you nuance when you have a buyer that doesn’t engage with how you are selling? (No sales BS)
  • You’re going to have to spend a lot of time making sure they understand the differences and explain why certain things are important.
  • Answer questions they didn’t ask in the RFP.
  • If selling into a fragmented industry where there isn’t a common view of the market,  how do you address that without doing a one-off view?
  • Typically before the sales call you know if they would be qualified for the product, but you haven’t discovered what they need specifically.
  • Meet the customer where they are, learn and establish your differentiated value
  • At IBM the first call was about them and the second call was all custom.
  • EX: Same product for utilities and retail, both had the same differentiated value of needing it to keep transactions going. The difference in the sales pitch was the example used at the end.
  • On your podcast, I’ve heard you talk about needing to reevaluate your positioning as time goes by. Can you talk about the mental difficulties of people changing their positioning?
  • Different at small vs large companies
  • Small company: We were panicking because we changed a product before we sold it to them, but customers didn’t care about the shift because they weren’t aware of the company previously.
  • Big company: Very difficult to make the switch at IBM because of how established they are and people still thought it was the old product.

10:30: Chris Mele: Investors, Pricing Science, and Optionality

  • Mastering software pricing is as important as product management
  • Pricing strategies such as pay as you go, etc. have been around for decades
  • The process of “marrying” with software is like a complex mating ritual
  • The traditional system design
  • Build a great product, gain some traction, get investment capital, grow your business
  • Credit crisis of corporate debt
  • Acquired 270K in debt because they did not understand the value of their software
  • “See one, do one, teach one”
  • Indoctrination method used in medicine. Surgeons have high rates of depression
  • Most businesses have no idea what to do with pricing, can be seen from:
  • Discount (%) vs. list price graph
  • Common cause: Partial usage agreements for higher discounts, signifying inefficiencies in packages
  • List prices vaporizes in discounts, net prices erode, pricing power disappears, buyers game the system, will copy competitors, price setting rarely happens
  • Typical solution: Build more product
  • 3 problems to solve to inject trust, uniformity and get maximum net price
  • Pricing model
  • Quarterly, annually, etc
  • Figuring out whether or not to give a discount/charge a premium for billing quarterly, annually, in advance
  • Same net price
  • Offering model
  • Combination of product features and services
  • Insights, analyzing things, Intellectual property
  • Licensing model
  • What’s the range of quantities you want to see on the sales floor (usage, percent of revenue, etc.)
  • Process the tree from the bottom up licensing → offering → pricing
  • Pricing discussion is meaningless if everything else isn’t completely figure out
  • Your pricing philosophy
  • Pricing consistency and uniformity leads to fair pay for your value
  • One person getting a discount leads to overall net price erosion; everyone wants the same discount
  • Market fairness pricing
  • If the customer is at center you are saying all customers are treated the same (consistent treatment)
  • Discounts are earned based on volume, not given
  • Pricing is a process, not an event
  • Must be iterated upon. Pricing needs to be constantly discussed
  • If you iterate multiple times a year, you will have a more optimized pricing strategy than competitors
  • Never misrepresent to get market intelligence
  • Sets a dangerous precedent in the company, starts a slippery slope
  • Explain your pricing philosophy to customers
  • Have a hypothesis you bring out into the market and then iterate over and over.
  • Your approach should produce a scheduled net price for everything you sell
  • Hold everyone accountable to land deals close to scheduled net
  • Always be raising net prices
  • Quarterly/cohorts raises


  • What is your view on introductory pricing and how do you go about it? What Type of discounts do you give?
  • Traditionally, beta is given to a corporation for free. Makes you think that a deal is close.
  • Instead, once you have a product you think people will use, you flip it into an early access program, even if you think it is beta
  • If you know the sea of price points, pick something on the high end
  • If you are not sure on a price, term limit.
  • Have an open dialogue, “how would you buy it?”
  • I like to have structures where I can get transactions, and there is transparency.
  • Try to understand how hard it would be to be able to extract the net price.
  • Trick: never ever license and addition of your software. Do not sell them the enterprise edition at the lowest price point. Instead fund your roadmap.
  • What do you think about having or not having sales rep commissions? Once they have a rep, they will try to push the price down with discounts.
  • In bamboohr’s case they went commissionless, it worked well for them
  • If you have a commissions program, don’t meander them too much on.., reward them on the scheduled net price they are getting
  • Our company sells standard software packages with standard pricings, and people see if it’s in their pricing ballpark. Our competitors require a long process to obtain a price, such as filling out a form or making a call. Which approach is better?
  • I suggest using something somewhere in between. The list price is different from the net price, have a minimum.
  • If unsure, go with list price or minimum, but not everything needs to be on your website

11:30: Jamie Woolf & Christopher Bell: Using Stories to Inspire and Drive Change

  • Building healthy culture bridges disconnection felt in the workplace, stories act as a bridge
  • Activity 1: What’s the one most important identity to you?
  • Who is the protagonist?
  • Mirror neurons, audience feels the way the story is
  • Feeling get stored into memory, emotional stories are memorable
  • Oxytocin and Cortisol, hormones that get released, causes people to act differently
  • Life is precious: personal story about alzheimer’s will make people more likely to donate
  • Bringing humanity into the workplace through stories
  • We’ve over-indexed on analytical, cerebral in the workplace. Extracted the joy.
  • Can build trust and connection
  • Show vulnerability and emotion in your stories, and people are more likely to relate and trust you
  • Bring meaning to your organization’s values
  • Empty words without stories
  • Inspire during hard times
  • Activity 2 & 3: Think about a pivotal moment in your life that was challenging, but informs who you are today.
  • Storytelling is a learned behavior
  • Most people are good at talking to others, but not telling stories
  • Stories are not mysteries, they can be put together like legos
  • What makes a good story? (What does a listener want?)
  • Great characters we can root for (Hero)
  • Doesn’t have to be a person. Can be emotions, software program, business
  • Great structure we can easily follow (Obstacles, Stakes, Dramatic Climax)
  • Conditioned to receive the 3-act story
  • Great purpose we can attach to (Victory, happily ever after)
  • What have we learned?
  • Seven Questions for a Solid Story
  1. Who is the hero of your story?                Once upon a time… (Hero!)
  2. What do they want?                                And every day… (Want!)
  3. What happens if they don’t get it?                Until one day… (obstacle)
  4. What is in their way?                                And because of that… (fail)
  5. How do they overcome that?                        And because of that… (overcome)
  6. What led to victory?                                Until finally… (Victory)
  7. And then what?                                And ever since… (Happily ever after!)
  • Answering these questions in 3 minutes results in a great story

14:00: Chris Spiek & Justin Dickow: How Autobooks Reinvented Itself

  • Small business owners want to focus on running their business, not doing taxes/accounting
  • Unique way taken to market: Autobooks is used through online banking, not the autobooks web domain
  • JBTD Research: Did interviews with small business owners on their experience:
  • What they found: couldn’t pay by credit card/paypal/square, only check
  • One of the clients said “they don’t use autobooks how you think I use it”, wanted more detailed invoices for large transactions
  • Invoicing company or company that doesn’t send an invoice
  • Small business owners give great insight to JBTD compared to big companies or consumers
  • Disintegrated the product: Separated accounting, invoices,
  • Think about getting paid more than accounting
  • Took 6 weeks to ship the wireframe, not quite on the mark – a common problem businesses struggle with
  • Talked to Ryan Singer, had radical views on how to build it. Asked very specific questions about the engineering approach which he could not answer.
  • “Kickoff meeting/The paper shredder” – Sliced and divied up product manager’s sentences into tasks.
  • Led to holes in complete product because engineers responsible for each task didn’t know the whole context
  • Every engineering decision has tradeoffs. Everyone focused on their tasks and not the broader picture.
  • Shape up: A new method
  1. Appetites                         instead of         estimates
  2. Fixed time + variable scope         instead of         fixed scope + variable time
  3. project assigned to a team         instead of         task assigned to an engineer
  • Resulted in focused, autonomous teams
  • Growth resulted in bugs, maintenance, etc. that meant they started slipping into their old ways (“I don’t have time to talk to you”)
  • The pile up
  • 4X sign ups with a simple UI change, 6 week appetite
  • Before you can receive the first autobook invoice, need to fill out a 55 question form
  • Response: add 4 weeks to your appetite and we’ll talk
  • Just fixing bugs will not keep the company afloat. Need to capitalize on this 5x growth opportunity
  • 30 minute product manager and engineer meeting: product managers began to ask engineers to de-risk things. Which created conflict later on.
  • Easy, but first we need to finish rebuilding …, migrating .., etc.
  • The break down
  • high emotion interactions, talking about problems not solutions, every idea is bad, too busy, You have more to figure out before we will commit to doing that
  • The duplicity problem: when the number of things you’re doing is greater than the number of people you have (leads to people doing nothing)
  • Engineers see their backlog of tasks as things they need to do, while project managers see it as a bigger problem
  • 2 Steps to fix this
  1. Set up the appetite up front – creating general bounds to solution and time to be used, then figure out what you can do in those bounds with said amount of time
  2. “What can we do in 6 weeks” instead of “We have a 6 week appetite”
  3. Dedicate a Senior Engineer to work alongside the product team
  1. Progress happens synchronously, all options are explored
  2. Output is an agreed path forward between product and engineering

15:15: Kyle Bazzy & Derik Sutton: Rethinking Sales From the Demand Side at Autobooks

  • Life before Demand Side sales (old way)
  • “I’m not working these leads. They are trash”
  • Lead →MQL→SQL→Dem→Proposal→Closed deal
  • Life after Demand Side sales (new way)
  • Demand side sales: marketing and sales understand each other
  • Establishing alignment with Demand side sales – customer centric approach
  1. First thought – “making space”
  1. Ask questions, Give stat, State obvious, Understand customer
  2. Old way: what can I put out so people will interact
  3. New way: working with product and engineering at booth to talk to customers
  4. “Candy marketing” vs “trail mix marketing”
  1. Candy: Short-lived (looks exciting/appetizing)
  2. Trail Mix: Healthy, takes you the full journey, build full content
  3. Passive looking – “learning how”
  1. Educating them and telling them how it offers true value to them
  2. Old way: 1:9 intro to full feature demo
  3. New way: 1:9 highlight reel demo to aligning to FI job
  1. More about conversing with customer, show that you care (ask why)
  2. Leads to real-time feed back for marketing To iterate through messages
  3. Have marketing team do sales, proximity creates empathy
  4. Helps learn how customer buy and get real time feedback
  5. Active looking – “see possibilities”
  6. Old way: after demo, prospect wants to now price, then they ghost you
  7. Encouraged to follow up constantly, but still get ghosten often
  1. New way: “the betting table” tokens given to sales reps to spend/bet on leads, aligns them to customer progress
  2. “(slide) Decks have legs”
  3. When customers ask for deck, you shouldn’t send them the original deck, send them a follow up deck
  4. They won’t be able to convince their execs of the same value that you’ve convinced them of
  5. Demo 2:
  1. 1:9 speaking to FI job: full feature demo →leads to a lot of miscommunication
  2. 100% alignment with all parties
  3. Deciding – “making tradeoff”
  1. Old way: begging
  2. New way: make a tradeoff: choosing best way to make progress instead of compromising
  3. First use – “making progress”
  1. Old way: “what are they saying”
  2. New way: mutually agreed action plan (maap), agreements on consequences
  3. Sales alignment across the organization is based on customer progress
  4. Lead to 10x customer growth
  5. Ongoing use – “building habits”
  1. Old way: one to one account management specialized by partner channel
  2. New way: growth teams aligned to customer progress post product launch
  • “Are you marketing and selling the way your

10-04 (Wednesday)

9:00: Claire Lew: Doing more with Less

Tons of things to do with limited resources. 7 points to actually implement things in your company:

  1. Question “More”
  • What – Doing more of the “right thing”: Revenue/Customers/Product
  • How – Should be good quality, fast, and cheap
  • Focus on the one thing that will result in the most leverage
  • Fast is typically most important in resource-constrained contexts
  1. Finding the quickest way to achieve your goal is important
  2. Pitfalls: Projects you are excited about/like doing/good at/feels like making progress/have always done
  • Do an activities inventory
  1. List out every activity/project/priority within the team
  2. “Does __ help us achieve __ quickly?”
  3. Figure out the “one right thing” to do: Make it clear to ourselves and our team
  4. On-the-Ground Pulse Check
  • How is your team actually feeling right now?
  1. No amount of wordsmithing will get people excited if they are exhausted
  • Questions to ask about
  1. To your leadership team: How confident the organization is focused on the right things
  2. To frontline managers: Is there anything you’re worried about being true that is starting to be true?
  3. To employees: What’s felt ost uncertain about the company
  4. Describe the Change in the Wind
  • Describing new projects can be “chilly”
  • “Now focusing on __ because achieving __ quickly is most important)
  1. Communicating just this is not enough– analogous to meteorologist describing why the wind is changing, but it is still cold
  • Need to explain Where it’s going, Where it’s coming from, and What the team should expect
  1. Simplifies the operational flow by explaining how to get on board
  • Example: “What’s most important and stays true is __. What we’ve learned is we need to achieve __ more quickly. To do this, we will focus on only __. This is how it will make an impact on you: __.”
  1. On-the-Ground Pulse Check Part 2
  •  Recalibrate how “chilly” the wind is to your team
  1. Hold 1:1 meetings to clear things up/get teams perspectives
  • Questions to ask about
  1. To your leadership team: Based on our new focus, what else should we prioritize, cut, or adjust?
  2. To frontline managers: Where do you anticipate friction in your team to accomplish our new goals?
  3. To employees: To what degree do you see yourself changing any of your day-to-day activities based on our new focus?
  4. Frameworks & Feedback (F&F)
  • Framework
  1. “We should do __.” → “Here’s a framework for thinking about __”
  2. Only way the team can move independently
  • Feedback
  1. “This is good + you’re on the right track” → “This is good + you’re on the right track because
  2. Do they have context as to why things are changing, or are they reacting to what you say
  • F&F enables scaling the mindset of doing more of the “one right thing”
  1. Scale the mindset
  • It’s hard to do “more of the right thing” if it’s only you doing it
  • 5 areas of focus
  1. Manager Mindset Shift – manager success is enabling your team rather than just getting work done
  2. Effective 1:1s – Frontline managers giving similar questions to their team
  3. Giving + Receiving Feedback – being able to tie everything to the company’s goals, etc
  4. Communicating Vision – make sure everyone’s on the same page
  5. Coaching
  6. Self Check
  • The pressure is real, and only increases
  • You need to regularly pause in order to reflect
  • “Slow is smooth. Smooth is fast.”
  1. How can I slow things down for myself to ultimately make the team go faster

10:30: Lauren Kelley: Meaning in Metrics

  • The rules have changed for SaaS (Software as a Service) companies
  • Growth at all cost → Profitable growth
  • Digital and cloud applications are going to continue growing
  • R&D investment of larger SaaS companies is going up
  • Fundamental Metrics
  • Indicators, not a diagnosis
  • Rule of 40: Growth rate + EBITDA should be close to 40
  • Not all 40’s are the same (35 % growth 5% EBITDA != 20% growth 20% EBITDA)
  • US SaaS companies growth rates are declining as P/E ratios are increasing
  • Unit economics
  • Profit/loss calculations per customer
  • GTM productivity
  • For every dollar in sales and marketing, how much new revenue are you generating
  • Want to be between 0.5 and 1.5
  • 0.5 and 1 is okay, not great, 1 to 1.5 is good, above 1.5 means you aren’t doing enoughStrongly correlated with revenue growth
  • R&D ROI
  • Take last years R&D spend, and calculate the change in revenue
  • Need to figure out whether or not R&D is producing new revenue
  • Use Benchmarking as a Roadmap
  • Numbers take the emotion out of arguments
  • FInding root causes of performance issues
  • Identify if KPIs calculations are correct
  • Prepare for budget, pre/post IPO, etc.
  • Gets the executive team and board on the same page
  • Benchmarking builds trust, accountability, creativity and problem solving
  • Types of benchmarking
  1. Internal benchmarking
  1. From internal systems
  2. Benchmark current performance against your own historical performance
  3. Peer benchmarking
  1. Benchmark you current results and plan based on what peers and competitors are doing
  2. Source: investors, banks, surveys, OPEXEngine
  3. Strategic benchmarking
  1. From OPEXEngine, investment banks, public financials
  2. Benchmark against world class organizations
  • Common benchmarking mistakes
  • Only use internal benchmarks or word of mouth/networking →Look to peer and strategic benchmarking
  • Compare apples to oranges → benchmarks varya lot based on size of revenue, sales/business model, etc
  • Data is not validated → Rely on validated data from real companies
  • Benchmarks are used for vanity → don’t hide from ugly metrics, use them to grow
  • Don’t take action → Consistently benchmark, aiming for regular improvements
  • Common SaaS benchmarking use cases
  • Margin expansion
  • How to get positive cash flow
  • Is our S&M, G&A, and how much we spend per person in line with our peers?
  • Growth efficiency
  • What is the value at stake?
  • How does sales productivity compare to other competitors & market leaders
  • Is the company under-investing in its sales?
  • Margin improvement/Cost management
  • Headcount accounts for 80% of SaaS company spendings
  • Use AI tools to increase efficiency
  • GTM (Go to Market) Efficiency Improvement
  • S&M efficiency + R&D Efficiency = GTM Efficiency
  • Don’t sell more than a one year contract, long contracts make companies less customer focused
  • Most highly valued cloud companies had S&M efficiency between 0.5 and 1.3
  • Get the cohort right, don’t focus on one metric

11:30: Greg Baugues: Someone Using AI Will Take Your Job

  • AI Anxiety
  • Existential anxiety (Terminator)
  • Ethical anxiety (AI music remixes)
  • Economic anxiety (machines will take our jobs)
  • Case Study: Chess
  • After losing to Deep Blue, Chess has become more popular than ever rather than dying
  • Chess players are the best now because they have been training with AI
  • Lichess offers free personalized improvements for every move, just 25 years after Gary lost to deep blue
  • Don’t Fear the Machines; Learn to work with them
  • Similar results in other studies: consultants are faster and more effective with the use of AI, than those who don’t use AI
  • Tools available today
  • Design
  • Midjourney
  • Can develop any images in any style
  • Removes the need for graphic design if its not needed
  • DALLE-3
  • Transcribe
  • AssemblyAI
  • State of the art speech to text
  • Transcription, summarize, speaker labels, and much more
  • Write
  • GPT 4 gives higher token limits 4000 →8000 or 32000
  • Can upload files to advanced data analysis in GPT
  • Can skip the writing step, skip straight to editing
  • Your Opportunities
  • Building with AI
  • Traditional: Search solution on google, paste the code
  • Everything on the internet is trying to steal your attention
  • AI Tools: Copilot, Cursor
  • Can get the ChatGPT API into your code
  • Build on AI
  • ChatGPT was revolutionary because of its UI, not the AI. The AI had been out for over a year
  • Your UI + Your Data
  • What is the special combination of these that will make your tool better than chatGPT
  • Descript
  • Edits videos based on transcription
  • Retrieval Augmented Generation (RAG)
  • Embeddings
  • Find vector embedding values for a bunch of text values store in->vectorstore

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