Episode 449 of The VentureFizz Podcast features Doug McNary, CEO of commercetools.
11 exits as a CEO or board member.
That is an incredible and extraordinary number, and that is Doug’s track record. You would be hard-pressed to find another executive with the same history of success, not only in the Boston tech scene, but also beyond.
He came up through the sales ranks to leading go-to-market organizations at high-flying tech companies like Tivoli and Motive before taking his first position as CEO of Onaro and he has been a magnet for success ever since.
Fast forward across multiple CEO roles and board seats, today Doug is the CEO of commercetools, the global digital commerce AI company that helps enterprises transform commerce for the AI era. More than 500 global brands, retailers, and enterprise companies rely on commercetools to power their digital commerce.
In this episode, we cover:
- Key advice on building a vertical AI company and why you must know your customer well enough to do their job.
- Advice for operators with aspirations to become a CEO and how boards evaluate candidate readiness.
- Lessons learned scaling software companies through major inflection points to successful exits.
- The evolution of eCommerce and AI’s impact.
- All the details about commercetools and how its API-native architecture positioned it for the AI era.
- The primary responsibilities of an effective board member and how to get on the radar for board seats.
- Crucial advice on building a repeatable enterprise GTM function, mastering outbound sales, and hiring top sales leadership.
- And more!
Transcript
Keith Cline: Doug, thanks for taking the time.
Doug McNary: Great to be here, Keith. Good to see you again.
Keith Cline: Likewise. I was excited when your PR firm reached out and asked to have you on the podcast. When I saw your name, I was like, “Wait, Doug McNary, of course. He’s a legend.” You have had so many great success stories through your career that I want to talk about, as well as what you are up to now with commercetools. This is a great opportunity to learn from somebody who has seen all the different shifts in technology.
A fun fact is that you and I worked together. People who follow this podcast might know—because I throw it in here and there—that I’m a recruiter. I help startups hire great talent in product management, marketing, and customer success. I helped you hire a great product leader at SmartBear many, many moons ago. So it’s great to reconnect.
Doug McNary: That was about ten-plus years ago, if I remember correctly.
Keith Cline: Sounds about right. I want to tap into your wisdom immediately. There are a lot of great, smart operators building companies and startups who may not be founders, but are working their way up and have aspirations to become the CEO of a tech company. You accomplished that. What advice would you have for those operators trying to reach that goal?
Doug McNary: The path to CEO can happen in many different ways. I typically see people coming up from either the product side or the go-to-market side, particularly around growth-oriented companies. I came up from the commercial go-to-market side. I cut my teeth in sales and then moved into different leadership roles. My advice to anyone would be to try to get as much operational exposure across different parts of the organization as you can. Pick a path—either go-to-market or product—and move up that path.
A lot also depends on the company you get involved with. Do they have a founder or co-founder who is strong on the product side and needs someone to help on the go-to-market side, or vice versa? That is where I see things work best. I don’t think there is a proven formula where you must do specific steps to become a CEO. A lot of it is also timing. For me, I was in the right place at the right time for my first CEO role, and that led into the next one.
Keith Cline: That brings up another point I wanted your advice on. How do you know when you are ready and well-positioned? Approaching it from another angle: you have been on many boards and served on CEO selection committees. How do you know from an outsider’s perspective when a candidate is ready to take on that leadership role for the first time?
Doug McNary: First, it’s about matching the current requirements of the company. Sometimes you need a go-to-market person to lead the commercial side, or a product person to drive product strategy. Make sure there is a match there. Where I’ve seen this go wrong is when there isn’t a match, or when you get two people who specialize in the same area, which creates conflict. It’s important to ensure a good balance between the team and the requirements.
Regarding when you are ready: you just have to make that first jump. I remember my first CEO role—I didn’t know if I was ready or not. It was a trial by fire, an exciting experience, and a lot of work, but you just have to jump in and give it your first try.
Keith Cline: Let’s talk about your career and foundational story going further back. Tell us about your background growing up and how you got involved in the tech industry and sales.
Doug McNary: I’m a Boston native. By the time I was in seventh grade, we had moved five different times, including twice overseas. My father was a salesperson, and his job required moving around quite a bit. That taught me how to adapt to and accept change, which has been a critical foundational element for me.
Another foundational thing was that my parents heavily instilled the value of hard work in my generation. Having a part-time job through school alongside athletics was a big part of my development and helped me looking forward.
When I went off to university, my father told me, “If you’re going to go to school for four years, make the most of it.” I ended up going to an engineering school, which was a challenge for me at the time, but I am glad I did it. I had no intention of becoming an engineer, but it taught me how to approach and think about problems differently.
When I graduated, I wanted to pursue a commercial go-to-market path. The other great piece of advice my dad gave me was: “Before you try to sell to people, go live in their shoes.” So I joined General Electric in a leadership program that moved me around for three years, learning many different aspects of businesses from the inside out. After that, I moved into software, which set me down my path in tech and sales.
At a foundational level, it’s about embracing change and putting the work in. People willing to put the extra work in are rewarded for it. Also, if you want to sell to or provide solutions to businesses, learn how they work first so you appreciate who you are selling to or building for.
Keith Cline: I have a lot of founders on this podcast, and I love founders who live the problem first before addressing it, rather than trying to whiteboard ideas during an AI platform shift in an industry they know nothing about.
Doug McNary: A lot of people I work with at various companies don’t truly understand how the customers or businesses they are selling to work internally. They don’t view things from the customer’s perspective—they view it from their own, creating a mismatch. It’s really important to have that customer-centric view.
Keith Cline: Where did you originally cut your teeth in software sales?
Doug McNary: When I finished the program with GE, they had a software business in Burlington, Massachusetts called MRP (Manufacturing Resource Planning), which was a precursor to ERP. I got involved there as a sales support engineer. I left there and went into hardware sales at a local company called Wang Computer, selling hardware into manufacturing and distribution industries. That’s how I cut my teeth on the sales side and got into tech.
Keith Cline: I’ve always wanted to know more about the Wang story. As a kid, I saw that massive tower in Lowell and heard how Wang, DEC, and other foundational companies built the Boston tech scene. I know more about DEC because there are more DEC alumni in Boston, but I don’t see as many Wang alum.
Doug McNary: A bunch of people came out of Wang. Probably one of the most famous is John Chambers, who went on to become the CEO of Cisco. Dr. Wang was a fascinating person—he invented magnetic core memory and held an infinite number of patents. Unfortunately, the company didn’t break away from proprietary word processors quickly enough. When PCs and open systems arrived, Wang didn’t evolve and got lost in that transformation, as did several other companies along Route 128 and 495. It was an incredible era.
Keith Cline: They dominated with word processors and mini-computers. So many foundational computing shifts happened then—Dan Bricklin with VisiCalc, Lotus 1-2-3, and early laptops.
You worked your way up into leading sales across a continuous flow of high-growth tech companies. Your LinkedIn picks up at Tivoli, which was an Austin-based company. How did you get connected with them?
Doug McNary: Tivoli was a great run. The company was Austin-based and led by Frank Moss, who became a great friend. Tivoli solved a very meaningful problem as organizations shifted from mainframes to distributed systems. We built a go-to-market machine around selling into large organizations. I was employee number 13 and the first salesperson there.
A local recruiter, Ed Tacus, connected me with Frank, and it went from there. That was an eight- or nine-year run. We built the business, took it public, and a year after the IPO, IBM acquired us. I stayed on for a year post-acquisition. That software division eventually turned into a $3 billion portfolio inside IBM.
Keith Cline: Then you went to Motive, which also went public and was acquired.
Doug McNary: A group of us came out of Tivoli to join Motive, which was also Austin-based. We locked in on the shift to home broadband and the infrastructure challenges that introduced for service providers and cable companies. We built that company up to a couple hundred million in revenue, took it public, and then Alcatel-Lucent acquired us. That was also about an eight-year run.
Keith Cline: You were selling to telecom and internet service providers like Verizon and Comcast—a very complex sales cycle.
Doug McNary: Both Tivoli and Motive involved complex, long sales cycles, typically taking six to twelve months in a high-touch sales model.
Keith Cline: The next chapter was your first CEO role at Onaro. How did that come about?
Doug McNary: Onaro was my first CEO role. It was a Boston- and Israel-based company in the storage management space, providing software that helped large organizations manage distributed storage environments. We competed against EMC and HDS as the challenger in the market. We built that business over four to five years, were acquired by NetApp, and our software became a core part of NetApp’s storage management solution portfolio. Our customers were large banks, financial institutions, and enterprise organizations with complex storage networks.
Keith Cline: Then you became an Executive in Residence (EIR) at Atlas Venture, which led into VKernel.
Doug McNary: VKernel was a similar situation: a founder-led company with a smart product leader who needed a partner to help scale the business. I came in as CEO. VMware was taking hold, virtual machines were becoming widespread, and managing resource utilization was critical. We built a product that helped organizations optimize their spend and resource allocation. Quest Software approached us, and we were acquired by Quest, which later became Dell Software. I spent a couple of years working with Quest and Dell post-acquisition.
Keith Cline: Stepping in as CEO for those two companies and leading them to acquisitions, what key operational lessons did you apply?
Doug McNary: It wasn’t just go-to-market—it was operational leadership combined with accelerating go-to-market. Founders often struggle with organizational challenges as a business scales, such as prioritization and making hard decisions. Scaling is as much about deciding what not to do as what to do, including which customers to focus on.
I believe in building sustainable, long-standing businesses that balance cost and growth. In both Onaro and VKernel, I partnered with a highly technical founding CEO to scale the business. Because we were disrupting incumbents in the market, acquisition opportunities came to us naturally through corporate development teams or business leaders reaching out to discuss synergies.
Keith Cline: When you joined SmartBear as CEO, was the intent to build value toward an exit?
Doug McNary: The investors had been in the business for over ten years and wanted to realize value while continuing to grow. We spent three years building value and scaling the business. When the investors felt it was a good time to explore options, we hired a banker and ran a formal sale process, which resulted in an acquisition by Francisco Partners.
SmartBear was a PLG-led model driven by inside sales and inbound leads, built around two large open-source tools used by nearly six million developers. We moved the company from Andover to Assembly Row in Somerville, where we were the first business in that development. After four and a half years and the Francisco Partners acquisition, I exited and transitioned into advisory and board-level work. That is how I initially got involved with commercetools.
Keith Cline: You joined commercetools as a board member and later became CEO. How did that transition happen?
Doug McNary: commercetools provides a platform that helps enterprise organizations optimize e-commerce capabilities to drive revenue and reduce operational costs. I joined as Chairman of the Board five or six years ago when Insight Partners made its majority investment. At the time, the business was under $10 million in ARR. Today, we are north of $200 million in ARR and one of the largest players in the e-commerce platform space.
About a year ago, the company hit an inflection point requiring adjustments in execution speed and adaptation to how AI was changing work. I stepped into the CEO role to accelerate that execution. We have made significant progress in embracing AI internally and applying AI features to help our enterprise customers.
Keith Cline: How is AI transforming e-commerce across B2C and B2B?
Doug McNary: There are two distinct buyer types: consumer (B2C) and business (B2B). On the B2C side, AI impacts discovery through LLMs and third-party agents. However, most consumers still complete transactions on brand websites. Across our platform, we power over 500 enterprise brands, processing 750 million orders and over $120 billion in gross merchandise value annually. We help merchants get discovered across channels and use AI to drive higher conversion rates, build better promotions, and automate operations.
We see the B2B space as having a massive transformational opportunity for AI because B2B involves complex products and workflows. For example, an HVAC technician looking for a replacement part can use agentic workflows to handle search, discovery, and purchasing seamlessly. B2B commerce automation is a major growth driver for us.
Keith Cline: What advice do you have for established software companies built before the AI wave that need to evolve to avoid disruption?
Doug McNary: The idea that AI is killing software isn’t accurate, but AI is transforming how software operates. At commercetools, our platform was built from day one with an API-native architecture featuring over 380 APIs. Because AI relies heavily on APIs, this shift plays directly to our strengths. For legacy architectures that aren’t API-native, it presents challenges regarding how they integrate into agentic or AI workflows.
Keith Cline: What is the origin story of commercetools?
Doug McNary: Our co-founder Dirk Hoerig was a commerce practitioner working inside a large German organization, REWE Group, when he identified the need to replace legacy monolithic commerce architectures (like Demandware or ATG) with a modern, cloud-native, API-first model. The technology was spun out of REWE, which is when Insight Partners acquired the asset to create an independent company. Later, Accel joined as an investor during a Series C round. Today, commercetools is fully cash-flow positive and self-sustaining.
Keith Cline: While commercetools originated in Germany, Boston plays a major role in its executive leadership.
Doug McNary: We have a major presence in Boston. Myself, our CRO, Chief Customer Officer, and CFO are based in Boston. We have around 100 employees in the US (with 50 to 60 in Boston) and a large development team in Germany. About 50% of our revenue comes from the Americas, which represents a massive growth opportunity for us.
Keith Cline: What are the company’s future plans for growth and hiring?
Doug McNary: Much of our upcoming hiring will focus on go-to-market across sales and marketing. On the product side, AI has allowed us to prototype and ship products faster with fewer resources. We will continue expanding our go-to-market footprint globally and across the Americas.
Keith Cline: How would you describe the culture and your leadership style at commercetools?
Doug McNary: We have evolved into a goal-aligned, performance-based culture centered on customer success. My leadership style is to lead by example and ensure complete organizational alignment around our core objectives. I prefer to operate in the background supporting the team rather than acting as the sole public spokesperson.
Keith Cline: You have served on numerous boards, including Logentries, Lakeside Software, and DealRoom. How does an operator get on the radar for board seats, and what makes an effective board member?
Doug McNary: For me, it came down to being a proven operator and building strong relationships with investors like Insight Partners and Polaris. Selecting a board member comes down to matching the specific domain or operational needs of the company at that stage. An effective board member balances the relationship between investors and executive operators, keeping everyone aligned while offering practical guidance on scaling operations and go-to-market strategies.
Keith Cline: What advice do you have on building a repeatable, scalable go-to-market function in today’s market?
Doug McNary: The enterprise sales environment has shifted from inbound/PLG models to disciplined outbound execution. Buyers and CFOs scrutinize discretionary spend closely. We execute on a framework of Pain, Impact, and Priority: identifying customer pain, quantifying its business impact, and making it a corporate priority to solve. Enterprise selling is a specific skill set requiring structured pipeline generation.
We break our sales process into three distinct stages: creating pipeline, managing pipeline, and closing. Sellers must maintain equal discipline across all three stages rather than swarming only on closing deals, which avoids the trap of inconsistent quarterly performance.
Keith Cline: When hiring sales leadership (CRO/VP of Sales), what do you look for?
Doug McNary: Alignment between the candidate’s background and your specific sales motion (enterprise outbound vs. PLG inbound), as well as cultural fit. We look for leaders who instill a disciplined, repeatable sales process—similar to the talent development models established at companies like PTC, BladeLogic, or Tivoli.
Keith Cline: Do you have any podcast or book recommendations?
Doug McNary: For podcasts, I enjoy Something You Should Know during walks. For books, I am a big non-fiction reader focused on historical perseverance. I recommend The Wager by David Grann and Undaunted Courage by Stephen Ambrose, which details the Lewis and Clark expedition.
Keith Cline: What do you enjoy doing for fun outside of work?
Doug McNary: I like getting outdoors, staying active, and working around the house. I put myself through college painting houses, and I still enjoy getting a paintbrush out to unwind—it’s very therapeutic.
Keith Cline: Doug, thanks so much for taking the time to share your story, your insights on commercetools, and your advice with us.
Doug McNary: It was great catching up, Keith. I appreciate the time and look forward to seeing you soon.
