Building AI confidence through small bets

What’s up everyone, today we have the pleasure of chatting with Jenna Kellner, VP Marketing at Workleap.

• (00:00) - Intro
• (01:14) - In This Episode
• (04:30) - How to Manage Marketing Tech Debt During Rapid Growth
• (10:10) - How to Prioritize RevOps Tech Debt Without Perfect ROI Models
• (14:23) - Reasoning Through Broken Systems and Imperfect Data
• (19:23) - How High Performers Progress Anyway
• (24:28) - How to Build Confidence With AI Through Small Experiments
• (33:06) - How to Use Exit Planning and Cost Benefit Analysis for AI Tool Selection
• (35:57) - First principles matter more than tools
• (38:59) - Why Staying Close to Execution Improves Marketing Leadership
• (45:13) - Why Critical Thinking Skills Drive Marketing Career Growth
• (49:33) - How to Build Business Judgment in Technical Marketing Roles
• (53:03) - Why Confidence Without Humility is Dangerous
• (55:47) - How Revenue Leaders Prioritize Daily Energy
• (59:49) - Growing up
• (01:01:10) - Book rec

Summary: Jenna is a VP of marketing that can talk about the weeds of messy systems, uncertain decisions, and personal growth. You can’t hide from it, every company accumulates tech debt as teams rush to hit revenue targets. She frames tech debt as a leadership responsibility and urges executives to reinvest in core systems when patchwork begins to outweigh building. If leadership doesn’t get it, the best way to prioritize it is to shape it as an opportunity cost and lost leverage that will drain revenue the longer we wait. In the face of AI uncertainty, she argues that judgment compounds faster than technical knowledge, and that the marketers who become indispensable blend business awareness, proximity to execution, and decisive action grounded in humility.

About Jenna

Jenna Kellner is Vice President of Marketing at Workleap and a revenue-focused marketing leader who has spent more than a decade building marketing teams and scaling companies. She brings experience across Enterprise, SMB, D2C, SaaS, two-sided marketplaces, venture studios, and other high-growth environments.

Her career spans senior leadership roles at Minerva, On Deck, RBCx, and Ownr, where she led marketing, growth, and revenue functions inside complex, evolving organizations. At RBCx, she served as Chief Growth Officer for Ampli and directed marketing and growth initiatives within a large financial institution setting. She has also co-founded communities such as GrowthToronto and Little Traders, reflecting her commitment to building networks and businesses in parallel.

Jenna operates with a strong sense of ownership and accountability, grounded in her belief that every challenge ultimately becomes her responsibility to solve. Recognized as a WXN Top 100 Women in Canada, she focuses on developing high-performing teams that connect strategy to execution and translate marketing into measurable revenue impact.

The Frankenstein Reality of Managing Tech Debt: How to Manage Marketing Tech Debt During Rapid Growth

You know it.. Most marketers are operating inside half-connected systems. No company has a pristine, perfectly synchronized tech stack. Even if they think they do, it doesn’t last. Growth creates pressure, and pressure produces shortcuts. 

Jenna has seen the same cycle in startups and enterprise environments. In the early days, teams build whatever gets the job done. They start in spreadsheets, layer on point solutions, wire tools together with lightweight integrations, and move fast because revenue matters more than architecture.

Those early decisions never disappear. They compound. Years later, larger organizations inherit layers of systems that were added at different stages of maturity. Tools do not scale in sync. One platform gets upgraded. Another stays frozen because a team depends on it. Reporting becomes an exercise in orchestration. Jenna recalls walking into an organization where a sales leader pulled her weekly report from eight separate tools. That routine consumed time, drained energy, and normalized operational friction.

“You have to Frankenstein your way through them to get the answers you need.”

That sentence captures the daily reality inside many marketing and revenue teams. Quarter-end reporting still happens. Board decks still go out. The numbers get assembled through exports, CSV files, manual joins, and late-night reconciliation. Leadership often tolerates the strain because revenue continues to land. But the cost isn’t super visible:

• Reporting cycles stretch longer each quarter.
• Forecast confidence erodes.
• Team morale dips as manual work expands.
• Strategic decisions rely on partial or inconsistent data.

So how do we get out of this mess? Jenna views this as a leadership obligation. Someone has to decide that cleaning house earns priority alongside pipeline generation. She describes working with a founder who paused other initiatives to repair core systems. The work moved slowly. It required budget discipline and uncomfortable trade-offs. It rebuilt trust in data and freed leaders from cobbled-together dashboards. She compares the stack to a house. Repairs never end, but neglect guarantees structural damage. Leaders choose whether maintenance becomes routine or deferred risk.

Key takeaway: Treat marketing and sales tech debt as a leadership responsibility, not an ops inconvenience. Schedule deliberate cleanup cycles, secure executive buy-in early, and protect time and budget to rebuild core systems before the drag on revenue, morale, and reporting compounds beyond control.

Prioritizing RevOps Tech Debt Without Perfect ROI Models

Just get buy-in to fix all of our tech debt… myeah… sounds great. Good luck convincing your leadership team who’s off chasing the next AI tool they just read about on LinkedIn. Just assign a dollar figure to it, doesn’t have to be perfect, just guestimate it. Someone is building a report by hopping across eight tools, copying fields, reconciling numbers. You can measure the hours. You can attach a salary. You still miss the real cost.

Jenna takes a different approach. 

She’s not a fan of squeezing every system fix into an artificial ROI model. She focuses on the role RevOps plays in revenue creation. She says it directly:

“The job is to enable sales and marketing to find patterns, to hunt better, to run better campaigns and plays, to drive stronger revenue.”

When RevOps becomes a reporting service desk, capacity shrinks. The team spends its energy on maintenance rather than momentum. The opportunity cost compounds quietly. High leverage work stalls, including:

• Designing sharper segmentation models.
• Identifying conversion bottlenecks across funnel stages.
• Equipping sales with data driven plays that improve win rates.

You feel the drag in slower experiments and reactive decision making. Pipeline velocity flattens. Leadership wonders why growth feels harder than it should.

The urge to quantify every hour saved can trap teams in defensive mode. You start arguing over whether saving ten hours per week justifies a cleanup project. You try to forecast the dollar value of future pattern recognition. That debate rarely captures the structural risk of lagging systems. Jenna frames it as a leadership judgment call grounded in timing and context. If headwinds are rising, if competitors are shipping faster, if your team spends more time patching than building, the signal is strong enough.

She points to industries that invested early in overhauling core systems. Airlines that modernized their tech stack gained operat...