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Business of Software USA 2025: Ideas, Laughter, and a Few Hot Peppers in Raleigh

The Business of Software (BoS) Conference USA 2025 has wrapped up three incredible days in Raleigh, North Carolina, marking our third year in the city and our first at The StateView Hotel.

This year’s event brought together founders, CEOs, product leaders and builders from around the world to connect, learn, and share real experiences about building enduring, profitable, and people-first software businesses.

The venue was new, but the BoS spirit was the same: honest conversations, practical insights, and an extraordinary sense of community (plus a few hot peppers, of course).

Oh. And this year, hot peppers were officially added to the BoS tradition.

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Inside BoS USA 2025’s Lineup of World-Class Founders and Leaders

The countdown is on: just 10 days until BoS USA 2025 kicks off on October 6 in Raleigh, NC.

The Business of Software (BoS) Conference USA 2025 brings together software founders, CEOs and emerging leaders who want to build profitable, enduring companies.

This year’s program zeroes in on the most pressing challenges SaaS companies face today: From scaling with clarity, to weathering economic uncertainty, to finding independence and making sense of AI’s impact on go-to-market strategy.

Here’s what to expect at BoS USA 2025: a world-class lineup of founders and leaders sharing unfiltered lessons, actionable frameworks and takeaways you can put to work immediately.

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Building a Company Differently: The Buffer Story

Most startups follow a familiar script: raise money, grow fast, and figure out the rest later. Buffer, the social media management company with over 1.7 million users and $4.25M in annual revenue, chose a different path.

At the center of this story is Joel Gascoigne, Buffer’s co-founder and CEO, who believed from the very beginning that building a company was not just about growth. It was about doing it the right way.

Joel first shared this journey on stage at the Business of Software Conference USA in 2014. Fast forward 11 years, and he is returning to the BoS Conference stage with a very different story to tell. Over that time, Buffer saw its annual recurring revenue dropped 20% over a four-year stretch, fought through the challenges, and rebuilt stronger than ever. Today, Buffer sits at new all-time highs with $22.3M ARR.

But to understand how they got here, let’s rewind to the early days.

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Dharmesh Shah’s Mistakes and Lessons Building HubSpot

Building a multi-billion-dollar company sounds glamorous. The reality? It’s messy, full of wrong turns, and often more stressful than it looks from the outside.

Dharmesh Shah, co-Founder and CTO of HubSpot, has spent more than 30 years in the software world. At Business of Software Conference, he shared some of the biggest mistakes he made along the way and what he learned from them. These lessons aren’t theory. They come straight from the trenches of starting, growing, and scaling one of the most well-known SaaS businesses in the world.

Here are a few takeaways that stand out.

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CED and BoS Conference Continue Their Partnership to Power Raleigh’s Tech Community

The Business of Software (BoS) Conference returns to Raleigh, North Carolina, October 6–8, 2025, uniting SaaS founders, CEOs, and product leaders from around the world. Over three days, attendees will hear from industry leaders including Jason Cohen, Joel Gascoigne, Chris Savage and others, and join in the “Hallway Track” conversations that move beyond surface-level advice to explore what it truly takes to build enduring, human-centered software businesses.

When BoS USA first came to Raleigh, one partnership helped make it possible and continues to fuel its success today. We’re proud to once again partner with the Center for Entrepreneurial Development (CED) for the third year running at BoS USA 2025.

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How to be Productive When You Have Kids (or other Distractions)

As leaders in the fast-paced software industry, you love your work but it shouldn’t define you. Like many of your employees, you also have family, hobbies, and community commitments that matter. The real challenge isn’t just productivity. It’s managing the constant barrage of distractions so you can fully show up for every part of your life. This has only become more critical with the rise of remote and hybrid work.

Valentina Thörner, Head of Remote at Klaus and an expert on distraction management, points out a common oversight: much of today’s productivity advice was written by people with full control over their time and space. Her experience as a mother of twins made her realize that the real issue isn’t productivity methods, but distraction itself. Every interruption can cost 15 minutes to recover – an estimate that feels generous when a six-year-old is nearby.

Even if you don’t have children, your teams likely do. Learning to manage distractions is essential if you want a company where people stress less and produce more.

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No Silver Marketing Bullets

No Silver Marketing Bullets

Are you looking for the big growth thing? A new marketing trick, methodology, tool, or partner that promises overnight scale, explosive growth, or miraculous efficiency gains.

You might be wasting your time.

There are no silver marketing bullets – and that’s OK.

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Breaking Silos with JTBD: One Framework, Every Function

In SaaS, speed is survival. But speed without the right direction is just waste in motion.

Bob Moesta, co-architect of the Jobs-to-be-Done (JTBD) framework alongside Clayton Christensen, offers a mindset shift embraced by companies like Apple, Intercom, and GitLab. It’s a lens that reframes product, sales, marketing, and even hiring around one question:

“What progress is someone trying to make, and why now?”

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Appreciation Dame Stephanie ‘Steve’ Shirley CH

We’re very sad to hear the news that Dame Stephanie ‘Steve’ Shirley has died at the age of 91.

Her story is nothing short of remarkable – a testament to courage, innovation, and heartfelt purpose.

From her beginnings arriving in England as a six‑year‑old Kindertransport refugee, she transformed personal adversity into a lifelong drive to build something meaningful. She founded Freelance Programmers in 1962, a pioneering remote‑only software company staffed almost entirely by women, long before remote work became commonplace.

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If You’re Still Leading This Way, You’re Falling Behind

Business today looks nothing like it did 20 years ago. Old ways of doing things just don’t work in a world where AI is changing everything, customers expect more than ever, and workplaces have been flipped upside down by things like COVID. Big companies have been overtaken by small, fast-moving startups and technology keeps changing the game.

So how do you lead in this new world? According to CEO coach Joe Leech, it’s time to rethink what it means to be a leader and become what he calls a “Modern CEO.” It’s not about small tweaks. It’s about changing how you think and lead.

Here are 8 simple lessons that today’s SaaS and software founders, CEOs, and leaders should know:

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How Amir Salihefendić Scaled Doist with Asynchronous Work

For many SaaS and software leaders, the pivot to remote work in 2020 presented an exciting chance to re-evaluate how their companies truly operate. However, this often led to an unexpected consequence: employees found themselves spending more time in video calls than in office meetings, leading to significant impacts on well-being and productivity. If “Zoom fatigue” and the constant pressure of being “always on” sound familiar, it’s time to explore a fundamentally different approach to work.

Amir Salihefendić, CEO and founder of Doist (the company behind Todoist and Twist), firmly believes that the future of work (whether fully remote, hybrid, or even back in the office) demands a new model of asynchronous communication. Doist itself has been remote-first since 2010 and asynchronous-first for many years, successfully scaling with over 120 people across 30 countries with no outside investment. This isn’t just about tools; it’s a “philosophy and a way to communicate”.

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Jason Cohen’s Permanent, Defensible Strategy

Have you ever felt like your team is full of energy, busy, and working hard but the company still isn’t making the progress you expect?

It’s a common problem: your team is moving fast, but in different directions. Like molecules in a glass of water – moving rapidly, yet the water doesn’t go anywhere. Without alignment, energy is wasted.

This misalignment shows up everywhere:

  • Support teams over-serve small customers.
  • Product teams prioritize feature requests from one big client.
  • Marketing crafts messages so broad they connect with no one.
  • Designers bounce between too many personas.

Everyone is optimizing locally. But the business as a whole isn’t moving in a single, powerful direction. That’s a strategy problem.

Jason Cohen - Permanent, Defensible Strategy

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Lightning Talks at BoS USA 2025 – Will You Be on Stage?

At Business of Software Conferences, some of the most surprising, memorable, and actionable insights come from the Lightning Talks.

These are short, sharp, 7.5-minute talks given by attendees on topics they care deeply about. No fluff. No long intros. Just insight, storytelling and impact.

And yes: Lightning Talks are back for BoS USA 2025. Applications are now open.

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Layoffs. Tight Budgets. High Expectations. Now What?

In today’s fast-moving business landscape, it’s a common scenario: you have the same ambitious goals and tight deadlines as before, but with fewer team members and tighter budgets than ever. Layoffs, budget cuts, and exhausted teams are a reality for many leaders, from CEOs to VPs of People. So, how do you achieve ambitious targets when resources are constrained? Claire Lew, CEO of Know Your Team (now Canopy), shares a powerful framework developed from over a decade of working with tens of thousands of people.

The core idea? It’s not about just piling on more work. It’s about being strategic, intentional, and empowering your team.

Here are seven practical steps to help your organization thrive in resource-constrained environments:

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Why Your Marketing Isn’t Working (And What to Do Instead)

In today’s competitive landscape, many businesses find themselves stuck in a cycle of slowed, inconsistent growth despite having access to huge amounts of data. You might be seeing crappy conversion rates, relying on generic customer profiles, and launching marketing campaigns that simply fall flat. This isn’t just a minor hiccup; it’s a symptom of a significant underlying issue: customer blind spots.

So, what’s really sabotaging your marketing and product growth efforts? Here are some “shitty realities” that might be holding you back.

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Storytelling That Sells

Insights from Stephen Steers’s Business of Software AMA

Stephen Steers is not your typical sales consultant. A world traveler, stand-up comic, and author of Superpower Storytelling, he’s helped companies close high-value deals by shifting their sales approach from feature-dumping to context-driven conversations.

At his recent AMA at the Business of Software Conference, Stephen dropped a masterclass in sales strategy, sprinkled with humor, honesty, and hard-won wisdom.

Here’s what you need to know.

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Why Tech Alone Isn’t Making Us Smarter

Insights from Jeff Szczepanski’s Business of Software AMA

At the recent Business of Software AMA, Jeff Szczepanski – CEO of Reframe Technologies, delivered a thought-provoking session that dissected the paradox of modern productivity: why we have more powerful tools than ever, yet seem to be treading water.

This wasn’t just another AI hype session. Instead, Jeff challenged us to think more deeply about how we use technology, what collaboration really means, and why context (not more code) might be the key to unlocking meaningful progress.

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Stakeholder Engagement: The Overlooked Superpower in Product Leadership

One of the most critical, and most overlooked, skills in product leadership isn’t technical or even strategic. It’s stakeholder engagement. As Bruce McCarthy puts it:

“Even the most perfect plan can fail if your organization isn’t aligned.”

Early in his career, Bruce launched a promising new product, only to watch it flop. Why? He hadn’t brought sales or marketing into the process. Despite achieving product-market fit, it failed on product-company fit. That experience taught him what so many leaders learn the hard way: if your stakeholders aren’t with you, your plan doesn’t stand a chance.

Bruce McCarthy - Stakeholder Engagement

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The Simple Storytelling Hack to Drive Action in Sales

Differentiating your products or services is key to scaling sales and becoming a dominant market player. But how can you achieve this in a crowded software landscape? According to Stephen Steers, a sales expert and author of “Superpower Storytelling,” at the Business of Software Conference, storytelling is a powerful way to make your business stand out, attract people, and turn them into customers.

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