Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Tom McCarty, CEO of OrgChart, to examine how SaaS leaders should think about AI — not as a future consideration, but as an operational commitment that needs to happen now.
This episode is for SaaS CEOs deciding whether to pilot AI cautiously or commit to it fully across their operations and product — and what that decision means for their teams, their velocity, and their competitive position.
Key Takeaways
- SaaS CEOs who frame AI as displacement will lose their teams. CEOs who frame it as optimization — redirecting people toward thought leadership and away from monotonous work — move faster and retain better.
- A product manager manually sifting through 500+ support tickets per month is not doing their highest-value work. AI surfaces the themes in minutes; the human decides what to build next.
- The window for easing into AI has closed. SaaS companies that treat AI adoption as a gradual temperature test will find themselves behind companies that have already submerged.
- Staying in day-to-day execution past the growth inflection point is the wrong problem at the wrong level — the CEO job shifts from solving today’s problem to setting the course two years out, and the transition must be deliberate.
- Over-engineered sales compensation plans create roadblocks. Two-element comp plans tied directly to revenue outcomes — with real discounting leeway — outperform complex incentive structures that require manager approval at every turn.
SaaS CEOs Who Deploy AI Now Build Advantages Competitors Cannot Replicate Quickly
McCarty’s position is direct: “I believe every single role in a SaaS company needs to be learning and embracing AI into their day-to-day work — figuring out how am I going to incorporate this in what I do.”
OrgChart reached more than 2,000 customers and roughly 60 employees under McCarty’s leadership since he joined in 2021. That growth gives him a practical vantage point on what AI adoption actually requires at the operational level — not what it looks like on a roadmap.
His core claim: SaaS CEOs who wait for AI tools to mature before committing are already behind. The companies building internal AI muscle now will arrive at the next inflection point with infrastructure and habits their late-moving competitors cannot close quickly.
SaaS CEOs Who Frame AI as Optimization — Not Displacement — Retain Their Best People
McCarty draws a clear line between how AI gets introduced and whether a team embraces it or resists it. The frame matters as much as the tool.
“The thing I talk to my team about is it’s not about displacement. It’s not about eliminating roles or things like that, but it’s about really optimizing our work for where we add the most value.”
The practical test he gives his team: separate the work that is monotonous, data-driven, and routine from the work where genuine thought leadership, creativity, and individual contribution are irreplaceable. AI takes the first category. People own the second.
McCarty makes this concrete with a product management example. OrgChart processes more than 500 support tickets per month. A product manager manually reviewing those tickets alongside Gong recordings and customer interviews to surface themes is spending most of their time on the analysis, not the decisions that analysis produces.
“If you could have a cloud instance on top of those things and you’re surfacing all those insights and you’re finding the common threads in minutes instead of in days or weeks worth of analysis — what we do with that next is where I think we can actually provide more genuine thought leadership and creativity to the product.”
The sequence matters: AI handles the synthesis. The human decides what it means and what to build.
This framing also resolves the retention risk. When a CEO communicates AI deployment as a way to free people for higher-value work — rather than as a signal that headcount is at risk — teams engage with the tools instead of working around them.
SaaS CEOs Who Delay Full AI Commitment Give Competitors a Head Start They Cannot Close
McCarty’s most pointed message is about timing. The period for cautious, incremental AI adoption has passed.
“We’re no longer in a stage where we can wait in. This is no longer the time to dip our toes in and adjust to the temperature. We have to submerge ourselves in this one and learn it quick.”
His reasoning is structural, not just competitive. SaaS companies face a dual pressure: they need AI to operate more efficiently internally, and they need to embed AI into their products to stay relevant to customers. Both requirements are advancing at the same time.
“Pure SaaS plays with no AI, I think, are going to be really hard to maintain in the years ahead.”
McCarty sees OrgChart sitting at an unusual intersection of this pressure. The company builds workforce planning and org chart tools — the same tools customers now use to plan how AI will reshape their own organizations. A reduction-in-force scenario and an AI deployment scenario are structurally similar: you are deciding which work gets reallocated, which skills become redundant, and where human judgment remains essential.
“If I’m going to go add 10 different agentic instances, what am I doing? What’s the goals? What am I replacing? And if I’m trading these headcount off, am I really sure I understand everything that’s happening within those?”
SaaS CEOs who delay this analysis internally — while their product teams are being asked to build AI features — create a credibility gap. You cannot lead customers through an AI transition your own organization has not worked through.
SaaS CEOs Who Shift from Player to Coach Create Room for the Company to Scale Past Them
McCarty’s AI commitment is inseparable from a broader shift he describes in how he thinks about his own role as OrgChart has grown.
When he joined in 2021, the company had roughly 20 people. At 60 employees and growing toward 70 or 80, the version of the CEO the company needs has changed.
“I need to be looking further downfield — setting that longer-term vision. It’s that move and that shift of being a player on the field to really coaching to looking at where do we really need to be in setting the direction for a couple of years down the road.”
The discipline he applies is deliberate: identify which function needs attention at which stage, pull in where needed, and resist the pull to stay in day-to-day execution past the point where it adds value.
McCarty measures this by asking a consistent question: what does the company — and the board — need from him most right now? That question changes as headcount grows, as the revenue engine matures, and as the product roadmap extends further out.
The answer shapes where he spends his time, not just what he works on. A CEO who remains a piece on the board at 60 people is solving the same problems at 60 that they solved at 20. A CEO who has moved off the board is solving problems the company will face at 120.
What SaaS CEOs Can Take from This Conversation
| Principle | What it means in practice | Named evidence from this interview |
| Frame AI as optimization, not displacement | Tell your team explicitly that AI targets monotonous and analytical work — not their roles. The framing determines whether people engage or resist. | McCarty introduced this frame at OrgChart before deploying any AI tools — and attributes the absence of defensive resistance or attrition tied to AI rollout to leading with the optimization message rather than announcing tools first. |
| Submerge, don’t wade | Treat AI adoption as a full commitment, not a pilot. The time for temperature-testing has passed. | OrgChart competes in both directions simultaneously — using AI internally and selling AI-enhanced workforce planning tools externally. McCarty credits the full-commitment posture with keeping the company credible on both fronts rather than falling behind on either. |
| Match your role to the company’s stage | Reassess what the company needs from the CEO every time the headcount or complexity tier changes. | McCarty made a deliberate transition from day-to-day operator to direction-setter as OrgChart scaled from 20 to 60 employees — and is already repositioning his focus for the next stage toward 80, before the company outgrows the previous version of his role. |
| Keep comp plans simple and trust your salespeople | Two-element comp plans tied directly to revenue, with real discounting leeway and no approval chains, outperform complex incentive structures. | McCarty eliminated manager approval requirements for discounting at OrgChart and tied discounting latitude directly to rep compensation — removing process gates that were slowing deals and giving reps a financial reason to close rather than escalate. |
Quotes from This Episode
- “I believe every single role in a SaaS company needs to be learning and embracing AI into their day-to-day work — figuring out how am I going to incorporate this in what I do.” — Tom McCarty, CEO, OrgChart
- “It’s not about displacement. It’s not about eliminating roles or things like that, but it’s about really optimizing our work for where we add the most value.” — Tom McCarty, CEO, OrgChart
- “We’re no longer in a stage where we can wait in. This is no longer the time to dip our toes in and adjust to the temperature. We have to submerge ourselves in this one and learn it quick.” — Tom McCarty, CEO, OrgChart
- “Pure SaaS plays with no AI, I think, are going to be really hard to maintain in the years ahead.” — Tom McCarty, CEO, OrgChart
- “If I’m going to go add 10 different agentic instances, what am I doing? What’s the goals? What am I replacing? And if I’m trading these headcount off, am I really sure I understand everything that’s happening within those?” — Tom McCarty, CEO, OrgChart
Frequently Asked Questions
How should a SaaS CEO communicate AI adoption to their team without triggering fear of job loss?
Frame AI deployment as a reallocation of work, not an elimination of roles. Tom McCarty, CEO of OrgChart, tells his team directly that AI targets monotonous, data-intensive, and routine tasks — the work that consumes time without producing the thought leadership or creativity that only people can generate. When a CEO makes that distinction explicit before deploying tools, teams engage with AI as a capability upgrade rather than a threat. The framing must come first; the tools follow.
When is the right time for a SaaS CEO to fully commit to AI rather than running pilots?
That time has already passed. McCarty’s position is that SaaS CEOs who are still easing into AI — testing temperature rather than committing — are giving competitors who have already submerged a structural head start they cannot close later. The pressure is double: SaaS companies need AI to operate more efficiently internally, and they need it embedded in their products to stay competitive with customers. Both requirements are advancing simultaneously, and delayed adoption compounds the gap on both fronts.
How does a SaaS CEO know when to stop being a player in day-to-day operations and start coaching?
The signal is whether the version of you the company needed at the last stage is still the version it needs now. McCarty reassesses this question continuously as OrgChart has grown from 20 to 60 employees, asking what the board and the business need from him most at each stage. When the answer shifts from execution to direction — from solving today’s problem to setting the course for two years out — the CEO who stays in daily operations is solving the wrong problem at the wrong level.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
