The Metric Most MOps Leaders Never Track

Most MOps leaders know exactly what their tools cost. Very few know how close their team is to burning out. Olena Dingeldein tracks both.

Olena spent nearly five years at FreshBooks, one of Canada's best-known SaaS companies, leading the marketing operations team through growth, layoffs, pivots, and everything in between. A team of five. Zero churn across five years. In this conversation she explains how.

Show up before you scale

When I asked Olena how she defines people-first leadership, she didn't reach for the obvious answers.

"It's not pizza parties, it's not the tools you're in, it's really how you support each other, how transparent you are."

The foundation she describes is quieter than most people expect. It's built in 1:1s. In the moments where she deliberately lets her technical expert correct her in front of a stakeholder. In the willingness to say "I don't know yet" before she's ready to say "here's the plan." That last one sounds easy. During organizational change, layoffs, restructuring, the kind of uncertainty that ran through SaaS for the last few years, it's the hardest thing to sustain.

When the team goes quiet

I've talked to a lot of MOps leaders on this podcast. Most of them have a version of the burnout story. Olena's framing stopped me mid-conversation.

"Whenever the team is complaining, even if things are tough and hard, if they're still making noise about it, I'm not too worried. But it's when they go quiet, it's when they lose hope. Those to me are the early warning signs."

Not silence as peace. Silence as surrender. A team venting about workload is a team that still believes something can change. A team that goes quiet has given up on that. The question she's really asking isn't "is my team happy right now?" It's "do they still believe this is worth fighting for?"

Nap time is a KPI

One of the ways Olena protected her team during the hard stretches was something she called nap time. Every Friday, 9 to 11 AM. Unstructured time. No deliverables. And yes, if someone wanted an actual nap, that counted too.

But here's what made it different from every "we invest in our people" sentence in a company deck: it was tracked. Her team protected 10% of annual sprint capacity for learning. Learning stories had a formal place on the JIRA board. They showed up in performance reviews.

The full capacity framework she ran against: 55% running the business, 15% keeping the lights on, and 30% building the foundation, which included tools, integrations, data clean-up, and learning time.

"You end up focusing on the stuff you're measured on."

Seven tools. Then 200.

Olena has one of the best tech stack stories I've heard on this show. When she started at FreshBooks, she kept asking for the schema. Nobody had it. So she drew it herself, expecting maybe seven main tools in the marketing and sales stack. After nearly a year of cross-functional conversations, support, sales, product, the website team, the diagram was done.

"Then we got to the end of it. It had over 200 tools, services, integration support tools. It's amazing when you really zoom out."

What came out of that exercise wasn't just a diagram. It was a weekly cross-functional meeting she called the GTM Input Forum. A standing forum where marketing, sales, support, product, and analytics could see what was coming before it launched, flag technical issues early, and stop being the last to know. Support loved it. Sales loved it. MOps finally had the context upfront to do their best work.

Start with the problem

The last part of our conversation was about tool evaluation. Her answer was as direct as everything else she'd said: start with people and process, not the tool.

She told the story of her team spending eight months setting up an SMS channel. Applications, short codes, governance models, team training. Before she asked the question nobody had asked first: what are we actually using SMS for? As a B2B SaaS company, nobody could answer it. The channel got set up. The budget got spent. The use case never materialized.

The lesson isn't about SMS. It's about what happens when you start with the tool instead of the problem. And why the most important question in any tool evaluation is often the simplest one.

The bottom line

Olena Dingeldein is the kind of leader who measures team health the same way others measure pipeline health. Not because it's easy, but because she's seen what happens when no one does. Zero team churn. Five years building the operational foundation at one of Canada's most recognized SaaS companies. A team that worked through layoffs and came out the other side still in the boat together.

"Being a people-first leader means prioritizing your relationships and showing up authentically."

Start there.

Find Olena on LinkedIn: linkedin.com/in/olenadingeldein