A guide for founders ready to step out of sales so their company can step up.
As the founder, you’re your company’s first salesperson, and regardless of whether you like it or not, it may seem as if this “sales thing” isn’t as hard as everyone says it is.
This is the founder’s advantage. Founders have credibility, relationships, deep product passion, and your name is on the door – instant trust and credibility.
But at some point, you’ll need to step aside and hand the sales baton to someone else, if you want to scale.
If you want your company to grow beyond the revenue you’ve been able to generate, you have to stop being the best and only salesperson in your company. Founder advantage is the reason your sales are working now and the reason they’ll stall out later.
Kristie shares some practical, founder-tested frameworks, not sales-guru fluff, that will help you unlock how to build a sales structure that will scale.
She walks us through:
- The question you must ask yourself BEFORE you hire.
- How to hire the right first salesperson for you.
- How your role as founder changes post-hire.
- Different approaches to scaling the sales function in your company beyond the first hire.
This is not a one-size-fits-all BS playbook – Kristie gives you the knowledge, tools, and frameworks to understand how you can build a playbook that works for you.
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Transcript
Welcome back from lunch. I’m Kristie Jones, the sales enchantress. Mark changed my title from founder of Sales Acceleration Group to the Sales Enchantress, and I’ve leaned in.
I have one question for you: is it possible for you all to scale your sales if you were not the primary seller? The answer is a resounding yes.
How many of you still think today that you are the best salesperson your company has ever had? And how many of you have tried to hand off sales to another individual and it has failed miserably? You are my people. We need to move from founder-led selling into something more sustainable for your company.
Today we’re going to talk about how you know it’s time to stop being the primary salesperson. We’ll cover hiring your first sales professional and what that should look like. And we’ll talk about scaling from one human to something different.
The good news: you’ve been set up nicely by other speakers this morning. If you only have one human to sell, you cannot boil the ocean. You cannot sell globally. You cannot sell into multiple segments. You have some real limitations.
So here’s the truth behind the magic of founder-led selling. The majority of my clients have founder-sold their way into about a million dollars in revenue or Series A funding. But there was a reason why they were able to do that. You gave birth to the baby. You know everything about it-what it likes, what it doesn’t like, its feeding schedule, when it needs to change its diaper, when it needs to go to bed. You know about the downsides of your product or service, and you probably found a pink bow big enough to hide those issues.
Your title alone gives you credibility that no one else has: founder, CEO, owner, president. Many of you have spent 10, 15, maybe 20 years in your industry. You have street cred. You have industry knowledge. You have a vast network of individuals. You know things that other people don’t know. Things your next sales professional won’t know.
The Founder Advantage: What Actually Works
Here’s my definition of founder advantage. You have deep product knowledge. How many of you built or were involved in building out your product? With that comes passion for your product. You don’t want anybody to call your baby ugly. And you know how to work around some of those issues that may be there.
You have credibility and relationships. You’re at the top of the food chain. You don’t have to talk to anybody to discount pricing, make an exception to terms or conditions, shorten or lengthen a sales cycle. No one has to go to you for permission, and you’re never going to say no to anything that might come your way from a prospect or a customer.
And there’s instant trust. People automatically trust you because you’re the owner, founder, president, or CEO of your company.
The Bottlenecks of Founder-Led Selling
But here’s what’s killing your ability to scale.
You overpersonalize the sale. You probably went through your Rolodex. You didn’t cold call anyone. You didn’t send a cold email. You maybe walked into a networking situation. In general, people you sold to knew you, or knew someone who knew you, and that referral gave you automatic trust, whether you knew that or not.
Here’s the real problem: they trust you. They don’t know anybody else at your company. They just trust you. They don’t actually trust your company yet. The moment they need to interact with anyone else, that trust evaporates.
You have zero process for handoff. You built the product. You sold the product. You may have even implemented it and onboarded customers. You’re the person they call when they have a question. They’re calling you, not customer service. And all of this is going to slow down your company’s growth because you’re taking customer service calls and not thinking strategically about your business.
And then my favorite: how many people here are control freaks? If I want something done right, I need to do it myself. That doesn’t scale, but I get it. If your first few customers trust in you, you’re going to have to trust in your team.
The Kristieisms
What got you here won’t get you there. I work with companies in the one to five million dollar revenue range. What got them to one million won’t get them to five. Won’t get them from five to 15. Won’t get them from 15 to 25, then 25 to 50 and beyond.
What I mean is that processes are going to have to change. Strategy may have to change. Every so many years or every so much revenue growth, you may see turnover in your team. The people that got you here won’t get you there. You’ve taken their skill set as far as they possibly can go.
I call this addition by subtraction. Sometimes the reason your company is not growing is that you have people in positions they’re no longer qualified or capable of doing.
Processes are something that’s almost always missing when I walk into a company. You are amazing founder-led sellers, but what you didn’t do during that entire time until you got to the million-dollar mark was write anything down. You had things that worked. You have best practices and strategies, but you probably don’t have any formal or written processes.
How on earth are we going to bring someone else in if you haven’t documented the playbook? If I say something important and you don’t write it down, it falls again and again and again.
You need a brag book. When things go right (particularly in sales, which is psychologically tumultuous), we need to write those things down. Sales teams only talk about things when they go wrong. But we need to document what works so that when things aren’t going well, you can refer back to that playbook and pull ideas you know worked before. Maybe they’ll work again, maybe they won’t, but at least you have somewhere to go.
Most of the founders I work with have zero culture of accountability. Sales reps don’t have quotas. They don’t have activity metrics. They don’t know their sales math. They don’t know what the average sale expectation is or what the close rate expectation is. You can’t hold people accountable if you haven’t given them expectations. And they need written expectations. You may have decided in your mind that they need to sell a million dollars in software, but they may not know it, or they may not know how you expect them to get there.
Signs It’s Time to Step Aside
How do you know it’s time to stop being the primary salesperson? If you’re VC-backed, the venture capital company will tell you when it’s time. Normally when they give you money. But if you’re not, it typically happens around 750,000 to one million dollars in ARR.
You’ve gone to the trouble to document what you were doing that worked along the way, and even what doesn’t work as well. You know your ICP and your buying triggers.
Identify what your swim lane is going to be. What segmentation are you going to own? I had a client in Romania called Yaw Rooms. Before the pandemic, they were selling conference software for tracking attendees and breakout sessions. Then the pandemic hit. They pivoted to workplace space software, because everyone needed to sit diagonally or six feet away from each other. The product started to sell itself. They reduced their sales force to two humans-one in North America, one everywhere else.
That was too much ocean to boil. Think about what you can own. What can a new person coming in and sell? Think about 50, 75, or 100 target prospects in this area. You’ve hit product market fit. You have repeatability.
You’ve probably been very uncomfortable as the seller. Mark pointed out earlier that a number of you are introverts. You don’t like sales. I’m a high D extrovert and sometimes I don’t like it. Asking people for money, asking for things you might not be comfortable talking about. All of this is uncomfortable.
These are signs you’re ready. But if every time you go to sell something you’re changing the pricing a little bit, or you’ve promised a customization, you’re not ready yet. If you still have a million dollars in pipeline but 750,000 of it is stalled, you’re not ready. If you’re still relying on friends and family, not ready yet. If nothing will close until you step in the room or get on a Zoom call, you’re not ready yet.
Here’s what it’s costing you to not stop founder-led selling. Obviously there’s lost revenue, but you’re also the bottleneck. You’re one human who isn’t doing the sales job 40 or 50 hours a week. You’re doing it in between everything else. You’re not touching as many prospects as you could. You’re not getting enough data to make strategic decisions about the product.
If you bring in a full-time seller, think about the exponential growth of information that comes with it. You’re also facing burnout and risk. But the biggest cost is delayed learning. You’re just not getting enough information.
Most of the founders I work with have someone scheduling appointments for them (an SDR, marketing, or an outsourced firm). They show up to do a demo and hopefully a discovery call. Then they don’t set the next appointment. Weeks go by. When I look at pipelines, the first thing I check is last activity date. Something else more important happened. You put out a fire. That follow-up call didn’t happen. Your sales cycle is probably a whole lot longer than it should be because of that delay.
The Messy Middle
This is where it gets complicated. We’re in the messy middle right now. Everything is different. AI happened.
I used to give the speech on transitioning from founder-led selling to hiring your first sales rep like I could do it in my sleep. But figuring out your sales team of tomorrow is not as easy as just hiring humans anymore. The tech stack is going to change. How humans sell work is going to change. It’s going to be a combination of things.
We still need humans, but the buyer is getting further and further down the buyer’s journey before they want to interact with anyone. A year ago, I would have said 70% of the way through their journey. Now I’m saying 90%. So online demos, your website, YouTube channels. They’re going to get information. You want to make sure they’re getting it from you, not just from ChatGPT.
We’re going to have digital agents. I was at a conference two weeks ago where someone who built a major software company said, “Everything is going to be an AI agent at some point, including leaders. AI agents are going to be buying from seller AI agents.” That made everyone uncomfortable. I don’t think we’re there in the near future, but we’re going to have to figure this out.
We need automation. If you’re not doing anything yet for your company, we need automation. AI note takers, CRM systems, all of that. But that’s just table stakes.
I think BI is going to be more important than ever before. I don’t think relying only on Salesforce or HubSpot dashboards is going to be enough. You’re going to have to layer on a BI tool. Your sales teams are going to need these types of tools as well.
Here’s my Christieism again: what got you here won’t get you there. That includes people, processes, tools, and strategies.
Hiring Your First Sales Professional
Let’s get really technical. Who is going to be your first sales professional, and what do they need to be?
There are different terminologies in sales. A hunter is someone who starts at zero every month. They go out into the wilderness, find a prospect, attempt to close them, and move on. They don’t implement. They don’t do onboarding. They don’t take customer service calls. They don’t renew anybody. They don’t do expansion. They’re your guns for hire. They’re wired for this.
A farmer loves to take the baby and help raise it. The hunter wants to give birth to the baby but doesn’t want to do any of the dirty work. They don’t care about kindergarten, graduation, or training wheels on the bike. Farmers live for all of that. They’re the relationship people. Cold calling breaks them out in hives.
Within farmers, you have account managers (reactive farmers) and customer success (proactive farmers). Customer success was born when SaaS started and everyone was doing monthly recurring revenue. VCs started investing like gangbusters. Then churn started to happen. VCs freaked out and said, “We can’t keep investing if there’s a hole in the bucket.” So customer success came about as a proactive role: someone working with customers to ensure value delivery, upsell, cross-sell, and expansion opportunities. It’s a different role than account management.
Then there’s the gatherer: someone who goes out and hunts, then is responsible for expansion, renewal, and keeping them happy. But you can’t be wired for both. They’re going to lean one way or the other.
For years, VCs would say your first sales employee should be a player-coach. I got so tired of hearing that I wrote a blog post with Bill Belichick’s picture. If player-coach is such a good idea, why isn’t the NFL doing it? I feel the same way about the gatherer. They’re going to lean one way or the other. You’re not going to get 50/50 out of them. But know what you’re going to get and what you’re not.
Over the last two years, I’ve been spending my time on full-cycle sellers. Most of my startups are hiring full-cycle sellers who prospect, work them through the sales cycle, close them, but don’t manage them afterwards. I’m spending less and less time hiring SDRs and more and more time hiring full-cycle sellers.
Traits vs. Characteristics
You need to understand traits versus characteristics. Traits are set by the time you’re 10 years old. You still have them today. If you interview people based on traits and ask trait-based interview questions, you’ll know that what you see today is what you’re going to see tomorrow.
For example, independence is a trait. Ask: “Tell me about the last time you created something for your prior company. Tell me about the last time you brought an idea forward.” Or: “When was the last time you made a decision without permission? When was the last time you did what you thought was right for the company or the customer, but you got your hand slapped for it?”
Other traits: manage-ability. I want someone who is a 7, 8, 9, or 10 on independence, and a 1, 2, 3, or 4 on manageability. But I want some manageability. A 10 in independence with zero manageability is a lone wolf. Probably not your first hire. But fourth or fifth, yes.
Other traits to look for: accountability, learner mentality. People who are readers are learners. Understand the traits you need, list them in your job description, and build your interview questions around them.
Compensation and Interview Process
You need a formal interview process. First, for apples-to-apples comparison. Second, for legal reasons. You need to do things the same way every time. The same people need to be involved throughout the hiring cycle. If you go to hire somebody else, you can change the people out. But you need a formal interview process and you need a scorecard so you can fairly evaluate and compare candidates.
Hiring is a two-way street. Midway through the hiring process, I flip the script. I say, “We now think you’re qualified to do what we think you need. Now we need to know if you like us, if you like it, if you can be passionate about selling this product or service, and if you think you can be successful.” The candidate will know way before you ever will if this is a good idea or a bad idea.
I spend about four to five hours total hiring a mid-market AE. They should know as much about you as you know about them before everyone makes a decision. They may self-select once that happens, which is fine. Make sure you’re not spending all your time questioning them. They should be meeting team members, asking questions, doing ride-alongs, sitting in on calls. Let them listen to recorded calls if you have them. Make them an educated consumer so nobody gets into a situation where they didn’t understand what they were getting into.
Compensation: The Money Conversation
Let’s talk money. Everyone here is in SaaS. We’re currently in a 50/50 base plus variable world.
The base should vary based on what your expectations are. If they’re going to sell $750,000, minimum bases these days are about $75,000. Anything at the one million dollar mark and above is definitely a six-figure base salary.
Commissions are running around 10%. I actually believe in doing other types of variable compensation. Sometimes I do what I call milestone bonuses. If your quota is a million dollars, every time they hit $250,000 you give them a bonus. The faster they get there, the more they’ll earn sooner.
I’m shocked how many times the money thing doesn’t surface early enough. I don’t want to waste my time or anybody else’s. If you’re expecting $120,000 and we’re prepared to pay $75,000, we need to know that up front. This goes back to having a comfortable conversation around money.
Onboarding and Development
When you get that A-player, do not just hand them a laptop and say, “Here you go. We’ve already logged you into the CRM system. Best of luck.”
I structure onboarding in four areas. I start by teaching them the industry. Then the product. Then the sales processes. Finally the tools. For each of these four areas, I teach it three different ways.
First, self-directed learning. If your CRM is HubSpot, there’s a certification. Everyone gets certified. Second, instructor-led learning. How do we customize the CRM system? What are our custom fields? How do we do things? What are our workflows? Nobody uses CRM out of the box. Third, on-the-job training. Partner them up with somebody. They need all three of these approaches plus ongoing training and coaching.
Who’s going to provide that coaching? Chances are you might be the first sales leader. A lot of my founders become sales leader number one because we can’t justify hiring a sales leader for one, two, three, or four humans. By the time the fifth person shows up, we’re probably ready to hire a VP of Sales. But not necessarily before.
The Handoff
Here’s where I get real candid. If you’re not willing to give the baby up to the adoptive parents and only get pictures at holidays and birthdays, you’re not ready. If you’re going to keep your hand in the cookie jar, constantly calling and asking about deals, you’re probably not ready to step out yet. And that’s fine. Someone’s got to do the selling. But no one wants to be micromanaged.
Get honest with yourself. We used to talk about cultural fit. I think that’s BS. For years I’ve been talking about cultural add (adding people to your team that don’t look like you, haven’t had the same experiences). But at this point, we care less about culture and more about skill.
Once you get the team to five or six, then maybe we can worry about culture. Right now you need revenue. You need to step out of the way. You need to find somebody who’s capable of doing that job. And cultural fit is not as important as someone who’s been there and done that before.
This is another Christieism: they need to be more willow than oak. When the wind blows, a willow tree stays standing. When a hurricane comes through, a willow tree will still be standing afterwards, but an oak tree will be uprooted. You’re probably still at a stage where iterations are happening. Pricing models might not be fixed. You might be playing with segmentation. You need someone with a high-risk profile, someone flexible. Not someone from Fortune 500 who had a process, a playbook, and a rule for everything.
Just because they potentially came from the industry, you still need to provide them training. Just because they’ve sold before doesn’t mean they’ve sold what you sell to your persona, in your ICP, or in your industry. And here’s something I get caught up in all the time: if you interview someone from the industry, you might think they’ll bring their Rolodex with them. But that Rolodex has all the people they sold at the other company who are still under two-, three-, or four-year contracts. What good is that going to do you?
Your New Role: Sales Leader
I had a founder several years ago who said something I’d never heard before: “I don’t know what I’m going to do when I’m not selling anymore. I don’t even know what my job looks like anymore.”
So what are you going to do when you’re no longer the first line of defense for sales? You’re going to be the sales coach and probably the sales leader. You probably aren’t qualified for it, but you weren’t qualified to sell in the first place. You figured that out. Everyone in this room is smart. You’re going to figure this out too.
Instead of managing deals, you’re going to manage people and processes. I cannot emphasize this enough: written processes, formal processes, changing processes, iterating processes, pivoting processes. You’re back to building your company.
You may get to be more involved in product. You may get to be more involved in fundraising. Maybe you have another business idea you want to test drive. Instead of being the face of sales, you’re building all the things that are going to help you step aside with confidence.
I don’t want you to step aside and feel like you’re handing the baby over to unqualified adoptive parents. We want to be able to hand the baby over with a mountain of notes. Just like you wouldn’t hand your baby to your neighbor without leaving pages and pages of instructions.
Scaling from One to Five
Now we have one human. You may not stop selling. If you hire a sales professional, you probably already have deals in your pipeline. Finish those deals. The best person to sell should be selling it. If you started that deal, you better finish that deal.
For a while it might be you and another person, but we need to make sure we have repeatable processes. Keep defining and redefining the ICP. In this new world, things are going to continuously change. Then see if you can replicate it. You did it. You got one other person to do it. You’ve both been successful. Can you hire two more?
Well, that documentation is key. Calls, recorded calls, whether on Teams or Zoom. Recorded demos. Now you’ve got some teeth. Now you’ve got things to share with other people.
Then you hire two more. And now you really do need a sales leader. You can stop playing sales leader and start playing true CEO. Hire a VP of Sales or CRO. Those individuals can take that group of five, make sure everything’s working together, that they’re doing the same things, that they have the same expectations.
When you’re really ready to scale (think 20 million, 30 million, 40 million, 50 million), you may need a sales ops person, a sales engineer, someone who’s looking at the data every day. They’re going to take BI tools, overlay them, run reports and dashboards. These people are probably the first to figure out when signals have changed, when something in the process might need to change.
What to Take Away
Before we go to Q and A, here’s what I want you to get out of today.
First, recognize what founder advantage is. Because when the first sales rep comes in, I get calls from founders three months later saying it’s not going well. I ask what that means. We laid everything out. They knew how many deals they needed to be adding to the pipeline every month. They knew the onboarding ramp. They knew the expectations. We laid it all out and it was very documented and very clear. And they say, “It’s just taking too long. I was doing it in 45 days, and they haven’t even sold their first deal, and it’s 75 days.”
That’s because you had founder advantage. Acknowledge that and understand it’s going to take somebody longer. It’s going to be harder for them. You may never have made a cold call or sent a cold email or written a cold LinkedIn message, but they’re going to have to do that. Their Rolodex, industry street cred, and network isn’t what yours is.
Second, understand where you’re going to go. What does your role look like now? It’s different. But how is it different? How do you want to impact the company now in ways you probably couldn’t because you were distracted before?
Third, think about what kind of systems, automation, agents, and humans you’re going to need. What’s that mix going to look like so that you can scale? I think there’s going to be fewer humans. For the last couple of years, I’ve been talking to my clients about stopping user-based pricing because as teams shrink, so will your revenue. You need to think about all the implications of AI and what’s coming.
Q&A
On Trait-Based Interview Questions:
Independence is a trait we always look for. Tell me about the last time you created something for your prior company. Tell me about the last time you brought an idea forward. When was the last time you made a decision without permission? When was the last time you did what you thought was right for the company or the customer, but you got your hand slapped for it?
I grew up in the Fortune 500 world as a buyer for Macy’s for eight years out of college. Our motto was get a partner. So I ask: when was the last time you made a decision with permission?
Independence: I want them at a 7, 8, 9, or 10. Manageability: I want them at a 1, 2, 3, or 4. I want some manageability, but I want independence high. Ten in independence and zero in manageability is a lone wolf, probably not your first hire. But fourth or fifth, I love managing a lone wolf. I love a little challenge.
Other traits: accountable people, people who are learners. It was mentioned earlier, readers are learners. Build your interview questions around traits.
On PLG to Sales-Led Growth:
Product-led growth is going to be more important to everybody, including B2B SaaS, because when the buyer gets to 90% on their own, you’re doing PLG without even thinking about doing PLG. That’s having videos on your website, YouTube channel, little five-minute feature functionality things.
You have to decide when to engage sales. What are the signals in the product? When an end user gets to X, when do you see traction? I had a client who gave their product to teachers for free. Once five teachers in a school, or 20 teachers in a district, adopted the product, sales called. They called the principal or superintendent. Once they felt like they had traction within X, if five people were using it, probably the other 25 teachers could use it too.
Think about the product signals and how many people in adoption within a particular organization.
On SDRs and BDRs:
You said you don’t like SDRs and BDRs because they add friction. But the economic argument is compelling: an SDR costs $100,000 and can support two sales reps instead of hiring three full-time AEs. Better economics.
If it’s working for you, if it isn’t broke, don’t fix it. I think the SDR/BDR role will probably be gone in two years. That’s my prediction. But if it’s a career path position, if that person can eventually be an AE at your company, then I’m all for it. The issue is that often there isn’t a career path. You say there is, but when it comes time to hire that person, you think, “Why would I take a chance on somebody who’s never sold before when I can take a chance on someone who has?”
If you’re using SDRs as a recruiting pipeline to real sales roles, that’s different. You’re doing that right. But it takes a lot of effort to move an SDR from setting appointments to working a full sales cycle. SDRs aren’t cheap anymore. Base salary is $60,000 to $70,000 now.
Also think about what your SDR is doing. If they’re just pimping the demo, saying “Would you like to have an appointment to see the product with my founder?” you can do that a whole lot cheaper. But if your SDR is disqualifying prospects (if they’re the first line of disqualification), then they’re doing real work. If they’re just pimping demos, you’re paying a lot for that. But if it’s working for you, don’t stop.
On Enterprise Selling:
Everything about enterprise is different. Enterprise is six figures or more, 12 to 18 month sales cycles, 10 to 12, 15 people involved within the prospect organization. That requires team selling. Sales engineer, customer success gets involved earlier, separate implementation team.
I’m happy to have that conversation online. The majority of people I work with, and I think the majority of people in this room, are probably not at that level. But yes, everything is different. Leverage your title. Pimp your title out, because sometimes you just need to show up to make sure that deal gets closed. In many enterprise cases, you have an executive sponsor-a C-level or high SVP assigned to a certain number of customers. You’re required to check in with them quarterly, executive to executive with nobody else in the room, because they’ve earned the right to have you care enough to do that.
Kristie Jones
Sales Enchantress
Kristie grew up in a ‘sales’ house. Her dad was the owner of a real estate company, mother a top 10% real estate agent and brother a successful Account Executive. Sales is in her blood.
Her sales career started at Gainsight where she created their first SDR team and then Brighttalk. For the past 20+ years, she has worked with small and mid-size companies, helping them expand their teams and grow their revenue.
Kristie brings over two decades of experience growing B2B SaaS startups and sales teams through hands-on coaching & consulting. Her specialties span sales process development, new business growth, customer retention, hiring top talent, and leadership coaching for founders and sales leaders. She’s the author of Selling Your Way IN, a blueprint empowering sales professionals to own their income and life.
Kristie grew up in Kansas and is a die-hard Jayhawk fan.
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