Life at UpKeep Episode 11: Jay Zandstra, Sales Enablement Manager

Life at UpKeep!

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"Life at UpKeep" is an employee spotlight blog series, where we showcase the amazing people and teams in our company doing amazing work together!

Through the eyes of our very own UpKeepers, you’ll get a glimpse into our company culture, our team’s big and small wins, how members of our team came to join and love UpKeep, and so much more! 

Meet Our Teammate!

[Image: jay zandstra, upkeep, sales]

We are excited to chat with Jay Zandstra, our incredible Sales Enablement Manager! Jay inspires us every day with his tremendous presence of passion and modesty in his work. Working with Jay has shown us how practicing compassion and humility is important in his role in supporting the Sales Team! We are humbled to have Jay on the team and admire the work he's done for UpKeep thus far. Here is his interview with our CEO, Ryan!

Ryan: What's up, Jay! Could you start us off by sharing what your role is at UpKeep, and some of your responsibilities?

Jay: Absolutely! I’m the “enabler” for all things Sales. On any given day I could be training new hires about the industries we work in, role-playing a discovery call, or working on Industry battle cards with marketing.

Any project we work on or develop with the Sales floor works on three key skills for a successful salesperson:

1. Sales Skill

2. Industry Knowledge

3. Product Knowledge

The challenge is when we work on these skills we need a tangible way to measure improvement. That’s where RevOps steps in with Curtis and Jeff helping build out the reporting and hypotheses for what metrics will improve based on the skills we develop.

Ryan: How did you find out about UpKeep? And, what made you want to join the team? 

Jay: I found Upkeep through Indeed. My wife and I just moved to California after living in Indiana for the last five years. We both wanted to live on the West Coast and agreed that five years after being married we’d move west. That five year mark was October 17, 2019. I came from the tech world in my previous role and really enjoyed working with clients to overcome their “fear” of technology and help them see the value of it. Technology has solved and continues to solve so many problems and the cycle of seeing a need, building a solution, and testing your solution I find scarily enjoyable. And, the UpKeep team embraces that challenge of building something that’s never been done before, and pushing so hard to make it perfect is a contagious mindset. It’s very brave. That attitude was obvious from my first phone call with Tyler.

Ryan: Currently, what’s a project you’ve been working on that you’re really proud of? Or, maybe a project you’ve already completed that you still think about?

Jay: I’m really proud of the work the RevOps team and managers have done with rebuilding the AE playbook. It’s a massive undertaking and is still in progress. We redesigned the Account Executive pipeline by simplifying the stages we walk our prospects through.

The problem we looked to solve was inaccurate pipeline forecasts and the hypothesis was that stages weren’t clear on criteria and that lack of clarity made it difficult to predict close dates. We changed the exit criteria for each stage and created more robust definitions for each stage. It was a group effort of Jeff, Curtis, Garris, Vala, and I to make the right changes and then manage that change to the Sales floor. Change management isn’t easy, but with the whole team on board with the changes, it continues to make progress and we are seeing results in better pipeline accuracy and better execution of our new stages. And when reps start to see those improvements, it’s like gas on a fire for motivation.

Ryan: What’s something you love about UpKeep?

Jay: It’s the people. One aspect of the enablement space is you are always collaborating. And that collaboration makes my job a blast. Between Henry/Ismail and the Product team to help with product insights to ensure the Sales team has the latest knowledge on any updates, Rebecca helping test rep’s in role plays, Arie and Victoria in Marketing to ensure any content we have on the industry is effectively shared and used by the Sales floor,  Heather and Angelique in the Operations team helping with our onboarding experience, Garris and Vala on the management side of Sales who ensure that Enablement is reinforced and supported in weekly standups. And, the Customer Success team for jumping into new hire sessions to help with Product setup trainings. Shoutout to Joe and Rachel.  Every time I need help from another part of the company, it’s always a “How can I help?” response. I also enjoy the critical aspect of our building sessions. If we are working on things and somebody thinks our way is wrong, it’s not a painful disagreement. It’s a constructive critique that comes from a place of wanting the best for the company and I haven’t always worked in that type of environment. It’s a great trait to have.

Ryan: Awesome, thanks again, Jay, for joining me in this episode of Life at UpKeep! 

Join us!

To learn more about our current openings, visit www.onupkeep.com/careers!