Leadership in AI Era: Olson on Building SaaS Teams That Last

The software industry is entering a period of reset, characterized by tighter budgets, accelerated AI, and heightened expectations for product quality. As a result, leaders are being compelled to reassess what scale, craftsmanship, and sustainable growth truly mean. Few executives have a clearer vantage point on this shift than Todd Olson, CEO and co-founder of Pendo.

Todd reflects candidly on how leadership must evolve as companies scale past $100M in ARR, why ‘courage’ -not just ‘curiosity’-is now a defining trait for executives navigating AI disruption, and how giving teams ‘access to the truth’ fundamentally changes accountability and performance.

He also offers a forward-looking view on how AI will fundamentally rewire products, engineering, and customer success into a more integrated model, while underscoring the fact that quality and human judgment will remain the ultimate differentiators.

Growth mindset and high-performance leadership

You’ve built Pendo from zero to 850+ employees. What leadership beliefs have helped you scale a global organization?

Olson: From day one, we were clear on our mission and values, and we’ve kept coming back to them as we’ve grown. One that really matters to use is having a maniacal focus on the customer. It shows up in how we prioritize, how we build, and how we make tradeoffs every day.

I’ve also learned that you can’t lead the same way at every stage. What worked at 50 people doesn’t work at 500. I’ve learned a great deal from peer groups and coaching over the years, which has helped me continue learning and adapting as the company evolves.

As we scale, my job is to focus on the tasks that only I can handle and ensure we’re hiring exceptional leaders for other roles. If you get the values right, stay close to customers, and put the right people in place, growth becomes a lot more sustainable.

What leadership traits do you now consider non-negotiable in executives who want to scale a SaaS company beyond $100M ARR?

Olson: At that stage, it really comes down to building and leading great teams. Executives need to hire well and often ahead of the curve, motivate people as the bar continues to rise, and be clear and consistent about performance expectations.

They also need the judgment to keep iterating without constantly changing direction. If you can stay focused, hold people accountable, and put your energy behind the few things that truly drive results, you give the business a much better chance to scale sustainably.

Leading through complexity and market shifts

SaaS is in a reset era, marked by AI disruption, tightening budgets, and shifting buyer expectations. What leadership behaviors matter most in navigating this next phase of uncertainty?

Olson: Beyond curiosity, leaders must be courageous. At some point, you’ll need to place some bets that are critical for the future of the company and (at some level) risk the current business. This is a classic Innovator’s Dilemma scenario, and you need to be a bit unafraid.

How do you prepare teams for AI augmentation without triggering fear, resistance, or the sense that automation is replacing craftsmanship?

Olson: I read a good quote early in the AI boom that addressed this, stating that people won’t necessarily be replaced by AI, but rather by people who utilize AI.

This is the future, and we need to all change the way we work. And ultimately, quality will win out. We’re already seeing that in the AI market as users switch between foundational models based on quality. Quality and craftsmanship drive adoption and ultimately win.

Q. What guardrails do you believe are necessary to ensure AI-driven development doesn’t degrade product quality or create opaque systems no one understands?

Olson: You need to measure it and iterate!

This is the exact reason we’ve invested in expanding our platform to measure agentic conversations and interactions. We’ve seen that AI requires training and adjustments to deliver on its use cases fully, so you need to ensure you’re measuring it to know how and what to change.

Culture and talent

How do you foster a culture where engineers, designers, and product managers feel deeply accountable for outcomes – not just output?

Olson: You give them access to the truth. When teams can see how people actually use their work, accountability becomes automatic.

They ship differently when they understand the real-world consequences of their decisions. That is part of why we invest so much in analytics and feedback. It democratizes insight, so everyone feels closer to the user and more responsible for the outcome.

Q. When you see teams slipping into underperformance, what leadership interventions actually reset ambition without destabilizing the organization?

Olson: Most teams do not fail because they lack talent. They can underperform when the end goal becomes unclear.

The reset usually begins by reconnecting them to the user’s problem and clarifying what success looks like. Once they see why the work matters, ambition returns. You do not need upheaval. You need focus.

Futuristic outlook

How do you see the relationship between product, engineering, and customer success evolving as AI takes on more operational work?

Olson: AI is going to fuse these teams more tightly together. Operational tasks will shrink, and cross-functional insight will grow.

Our newest analytics work is designed for this future because it enables teams to view the digital experience through the same lens, allowing them to address issues before they escalate and build on what works. Customer success will spend more time on strategy, product will iterate faster, and engineering will focus on building high-impact systems rather than chasing one-off issues. It is a more collaborative rhythm.

If you were starting Pendo today in an AI-native world, what would you build differently – and what would you build first?

Olson: Today, Pendo requires some level of effort to get up and running.

We’re looking at ways we can reinvent our product experience to be more autonomous and automated.

What leadership qualities will define the next generation of durable SaaS founders – especially as the pace of technological change outstrips traditional playbooks?

Olson: Founders will need to stay curious, be comfortable with rapid change, and treat data as a creative partner rather than just an audit trail.

They will build cultures that feel more like craft studios than corporate machines, grounded in iteration and real user understanding. The ones who endure will be the ones who can pair AI-driven speed with thoughtful, human-centered product judgment.

Any advice for future leaders?

Olson: I would tell future leaders the same thing I remind myself: build for real humans, not abstractions. Keep your craft sharp, stay curious, and surround yourself with people who make your ideas better.

Every venture I have been part of succeeded because we listened hard, iterated quickly, and stayed rooted in the community around us. Leadership does not change in an AI era. Your job is still to create a place where people feel energized to build great things and where the work feels worth doing.

Key takeaway from the interview

Here are a few key takeaways from the interview:

Leadership must evolve with scale

What works at 100 people breaks at 1000. Sustainable growth stems from clarity of values, hiring ahead of the curve, and leaders focusing on the things they can do uniquely.

Customer truth drives accountability

When teams understand how customers actually interact with their product/service, accountability naturally shifts from output to outcomes – without requiring heavy processes or micromanagement.

Courage is now a core leadership skill

In an era defined by AI disruption and market resets, leadership skills must evolve in 2026 and beyond. Leaders must be willing to place thoughtful bets that may challenge today’s business to secure tomorrow’s relevance.

AI augments people, not craft

AI enhances people, not craftsmanship. Teams that use it to learn and grow faster while protecting quality and judgment will win.

Measurement keeps AI accountable

If you can’t see how AI behaves, you can’t improve or trust it.

Clear message: AI scales work; leadership scales impact.