Thanks for stopping by.
I’m a techie empty-nester mom with deep B2B experience, an MBA, and a recent career reboot at a fast-paced fintech. I’m not your typical CSM candidate, but I bring a strong mix of strategy, execution, and a bias to action.
I’ve also been enjoying AI — enough that I went ahead and automated part of your talent screening workflow. The interview assistant below gives you a quick, interactive pre-read on my experience.
You can also test drive a lightweight Pendo tag audit app and review a larger concept I’ve been noodling to help demystify confusing account activity. They’re outcome-oriented and they reflect how I think: practical, customer-focused, and a little scrappy.
I hope something here resonates. If it does, I’d love to connect.
P.S. I’m looking for a hybrid opportunity in NYC.
About Ask Jenna
I developed this nifty tool in Lovable. It’s trained on my resume and story library — but if it tells you I’m an astronaut, feel free to double-check.
My lightweight app for auditing Pendo tagging
AI is only as good as the data behind it.
In Pendo, inconsistent tagging breaks natural language queries—making it hard to trust what you’re seeing. I built a lightweight audit tool in Lovable that ingests a Pendo export, checks it against a defined naming system, flags duplicates and gaps, and provides clear fixes—so the data is actually usable for analysis and AI.
My concept for a Customer Narrative app
the context layer your team is missing.
A good friend of mine from Scotland will often ask, “What’s the gossip?” Now, he isn’t asking for the dirt. He wants to know what are the human factors that are moving your life in one direction or another.
As I’ve been thinking about moving into a Customer Success role, I keep coming back to how hard it is to see the full picture of an account—not just the data, the events impacting the people. Drawing conclusions on data alone has inherent risks. To bring this to life, let’s use another complex ecosystem as an example: high school.
- The fact: a forward on the varsity soccer team made no goals at the start of the season. The story: she sprained her ankle and missed the first three games.
- The fact: A student failed his AP US History exam. The story: his grandfather was in hospice the week before and he was distracted.
- The fact: the musical’s second act was terrible. The story: the director left the production for the last three weeks of rehearsal.
Facts can lead us to make incorrect assumptions. Stories help lead us to the truth. But, most of the account story is scattered across platforms or lives in people’s heads. I’ve been sketching out what an app might look like if that narrative were brought to life in one place.
This concept for a Customer Narrative app would connect product usage, support activity, and call transcripts with human context—like stakeholder changes, internal sentiment, or company events—all time-stamped for alignment.
The result could be a living timeline that a team can use to understand the true dynamics at an account and how these dynamics fuel events and activity.
- Walk into QBRs with a clear, shared understanding of what’s changed and why
- Spot risk earlier—even when the humans aren’t saying what the data reflects
- Identify the moments when expansion conversations are most likely to land
- Bridge transitions between Sales, CSMs, and TAMs without losing critical context
Instead of reacting to isolated signals, teams could read the full story—and take action at the right moment.
© 2026 Jenna Wilkinson. All rights reserved.