This week, the Business of Software (BoS) Conference descended on Raleigh for the third year running. Having taken place the last two years at the Martin Marietta Center in Downtown Raleigh, the event migrated this year to The StateView Hotel.
The fresh venue, as well as general year-to-year change, made for an interesting blend of the familiar and the new at this year’s BoS.
On the familiar front, the conference once again represented a successful effort to connect a diverse blend of speakers and attendees from around the world with the tech ecosystem right here in the Triangle. BoS CEO Mark Littlewood (who presides over the program) is quick to sing Raleigh’s praises, and CED and Bill Spruill once again partnered with the conference to provide local support.
As was the case in 2024, CED also awarded scholarships for local founders to attend the conference. Founder scholars included Meghan Corroon (Clerdata); Austin Webb (Troupe); Joel Bush (Repspark); Andrew Knight (Cycle Labs); Mitch Heath (Teamworks); Joe Torres (One Care); Kevin Fowler (PublicInput); Vitaliy Levi (Gondola); Taylor Wright (Doculingo); and Jeremy Freeman (Allstacks).
As for what felt new, aside from the shift in venue, it was the makeup of the attendee crowd that stood out. In 2024, the gathering at the Martin Marietta Center had a distinctly international crowd thanks in large part to a heavy contingent of Canadians.
To be sure, this year’s event still boasted a crowd from all over the place, including many international travelers and one speaker who arrived on a motorcycle all the way from San Antonio. With Canadian travel to the U.S. in sharp decline, however, the international contingent was lighter—and the local crowd at least seemed to comprise more of the conference.
On that point, Littlewood expressed enthusiasm (and a bit of bewilderment) for BoS’s ability to forge new connections even between people who already live in the same ecosystem. To that end, he cited one extraordinary example:
“What’s fascinating here is… there are five CEOs, based in Raleigh, of companies with more than 20 million dollars revenue, who are here, today, who have met each other at Business of Software.”
That was pretty shocking to hear given the sheer number of tech ecosystem gatherings we have in the area. But ultimately it speaks to one of the main benefits of this conference establishing a place in Raleigh.
Oh—and also new this year was the introduction of hot peppers from up and down the Scoville Scale, ranging from the humble poblano right up to the dreaded Carolina reaper.
In a sort of play on the popular series “Hot Ones” (wherein the host and a celebrity guest eat progressively hotter wings over the course of an interview), Littlewood spent the conference sharing peppers with speakers as they exited the stage.
(He roped me in for a double-cheers’ing of, I think, cayenne and Scotch bonnet, which went over more or less okay until I accidentally scratched my eye and briefly left the solar system.)
BoS Conference Format
For those who are not familiar with BoS, the conference is best described as a multi-day, single-track event for founders, entrepreneurs, and others from the broader tech community. Rather than focusing on divided breakout sessions and in-the-weeds subjects, the conference consists primarily of a series of talks and other on-stage sessions with accomplished figures from around the U.S. and the world.
These speakers boast expertise in everything from marketing and storytelling to growth strategies and human ingenuity in the age of AI. Notably, these speakers also made themselves available during open networking sessions throughout the conference.
This year’s program also included “Birds-of-a-Feather” discussion tables during breaks and meals and a “Lightning Talks” session during which five speakers rolled through 15 slides each—with the slides set to advance after just 30 seconds each.
Below is a rundown of the speakers and topics that were featured at BoS 2024.
2025 Speakers and Topics
Day 1
- Jason Cohen (Founder & CIO of WP Engine) on “Escaping the Growth Ceiling.” Following opening remarks from Mark Littlewood, the program began with Jason Cohen discussing some of the biggest obstacles that cause virtually all companies to experience slowing growth at one point or another—and how to tackle those obstacles. Key Insight: Companies driven by a mission do better, and “all the people [at your company] deserve to grow.”
- Chris Savage (Co-Founder & CEO of Wistia) on “Building Beyond the Investment Next Round.” This was a sort of follow-up to a BoS 2022 talk about Savage’s decision to raise $17.9M debt to buy out his investors. This time around, Chris discussed the competitive advantage he and his company gained through independence and the ability to build as a family.
- Georgiana Laudi (Co-Founder of Forget the Funnel) on “AI’s Impact on SaaS Go-to-Market Strategy.” A returning speaker from 2024 (when she covered how to drive customer retention), Laudi had a multi-faceted presentation this year. What it largely boiled down to, though, was how teams can adjust go-to-market strategies when AI is providing everyone with the same tools for efficiency, messaging, and more. Key Insight: “Be a painkiller, not a vitamin.”
- Kristie Jones (Sales Enchantress) on “Overcoming Founder Advantage – Building a Sales Team That Scales.” True to form as the “Sales Enchantress,” Kristie Jones appeared with a wand, long gloves, and a cape to discuss common hiring missteps (such as hiring too soon, hiring for culture above skill, and more).
- Joe Leech (Founder of Mr Joe) on “Designing Your Ideal Leadership Team.” This talk revolved around the idea that leaders often underinvest in fostering or supporting leadership in others. Leech specifically covered the process of building a team of leaders as an alternative to simply gathering subject matter experts.
Day 2
- Claire Lew (Founder & CEO of Canopy) on “The Blind Spots That Break Us.” This talk wound up revolving largely around gaps and misunderstandings relating to AI adoption, and what they say about strategy more broadly. Lew covered transitions to AI usage in a practical manner, explaining that compressed change coupled with uncertainty yields blind spots. Key Insight: Per a quote Lew relayed, “The biggest barrier to AI adoption isn’t technology, it’s organizational change.”
- Chika Emebo (IDR Solutions) and Mark Stephens (IDR Solutions) on “When Four Words Collide – Turning Generational Diversity Into Your Superpower.” In a talk that echoed much of what we discuss on a near-daily basis at GrepBeat HQ, Emebo (Gen Z) and Stephens (Gen X) offered a combination of comic relief and insight on how to approach generational diversity on teams.
- Joel Gascoigne (Founder & CEO of Buffer) on “Navigating A Multi-Year Decline To New All-Time Highs.” This talk differed from most at BoS in that it was largely the story of a single founder’s specific journey. Gascoigne was refreshingly open and candid, however, in walking the room through his company’s precipitous decline (down 20% in ARR over four years) and the ensuing rebound.
- Amir Salihefendić (Founder & CEO of Doist) on “Invisible, Essential, Inevitable – AI Where It Matters.” To cover the broad topic of AI products, Salihefendić weaved together glimpses of his own company (and its new “Ramble” feature) and general insights. Most notable was his emphasis on digging beneath AI to focus on process (sharing playbooks with employees) and results (showing customers the value, not just the AI). Key Insight: “Don’t ship ‘AI for AI’s sake; ship outcomes.”
- Lightning Talks
- John Knox (Founder & CEO, Moving Average) on “The Introvert’s Guide to Networking: The Hidden Growth Lever.” Wherein Knox favorably compared Princess Leia’s networking approach (“Help me Obi-Wan Kenobi”) to blind use of The Force.
- Ivan Barajas Vargas (Founder & CEO of MuukTest) on “Top 15 Reasons the Vibes are Off With Vibe & AI-Assisted Coding.” Per Vargas, vibe coding is like using a chainsaw: great if you know how to do it, a bloody mess if you don’t. (Editor’s note: Ivan Barajas Vargas is a former Friday Nooner guest!)
- Art Koenig (Founder & CEO of xGEL Data Systems) on “Land and Expand? Oh, Really Now.” Art aptly pointed to D-Day as a relevant example of the power of strategic coordination. (It was also he who arrived via motorcycle from half way across the country.)
- Raj Mahajan (Founder of Jaan Capital) on “Fragile Deals: Enduring Lessons.” Like Joel Gascoigne before him, Mahajan offered a candid reflection of his own experience—in this case with a would-be exit that fell through and the steps that led to success thereafter.
- David Robison (Founder & CEO of Design Master Software) on “How to Hire Your Next Employee.” Wherein Robison provided insights on modern hiring and delved into his preferred trick of requesting video submissions from candidates (and why this works).
Day 3
- Pierre Chamberland (Founder & CEO of Netgovern) on “Just Make Everyone a Shareholder.” This one was in the title. Chamberland spoke at length about the various benefits to structuring a business such that employees are shareholders. It was an excellent talk, though the key insight from this one came from Mark Littlewood, who called out from the crowd that “As long as it’s completely fatuous and beside the point, AI is great.”
- Chris Mele (CEO, Software Pricing Partners) in conversation with Bill Spruill (Co-Founder & CEO, Global Data Consortium) on “The Price of AI.” This one was all in the literal interpretation of the title. That is to say, it was not about some societal price of engaging with AI, but rather about how to go about pricing AI-related products.
- Bruce McCarthy (Founder, Product Culture) on “Evolving Clear Strategy From Emerging Vision.” Bruce McCarthy closed out the conference by speaking essentially on how to spur growth by empowering product vision. Noting that initial processes and strategies usually run out of gas at some point, he discussed vision-driven product initiatives as a means of getting the flywheel going again. He also worked in an aside about his elaborate at-home coffee-making processes, and was then nearly deleted from existence by whichever hot pepper he chose to eat with Littlewood.
That pretty much did it for Year 3 in Raleigh. Below are some more photos from the event.
