Relentless, Relevant, and Ready: Orion Ascent Recap with Jessica Perez
Episode 135: This week, Kyle Van Pelt talks with Jessica Perez, VP of Growth at Milemarker. Jessica brings a boots-on-the-ground perspective to the wealth management technology space, working directly with advisory firms to help them unlock the full potential of their data.
Kyle and Jessica recap key lessons from the Orion Ascent conference, where the central theme was “Relentless”—a mindset focused on continuous improvement across technology, client experience, and firm operations. They discuss how advisors can avoid the overwhelm that often follows large industry events and instead identify one or two meaningful priorities to pursue. Jessica also shares her perspective on evaluating technology partners, embracing innovation like AI without chasing every trend, and focusing on the changes that truly move an advisory firm forward.
In this episode:
(00:00) - Intro
(01:28) - Orion Ascent recap
(03:15) - How advisors can apply a relentless mindset without getting distracted
(07:29) - The "AI frenzy" and improving client experience through smarter technology
(10:29) - How AI conversations are shaping advisor technology strategy
(13:24) - From tinkering to transformation
(15:02) - Evaluating whether technology vendors are true partners
(20:11) - Why data sharing and integration matter more than ever
(25:08) - Turning conference inspiration into real firm improvements
(38:43) - Jessica's Milemarker Minute
Key Takeaways
Be ruthless about technology partners that don’t truly help your business. If a platform doesn’t share data well, integrate with your ecosystem, or actively help improve your client experience, it’s worth reevaluating that relationship—even if switching tools feels painful. Technology vendors should function as partners in growth, not just software providers. 
Don’t chase every new idea after a conference—pick a few and pursue them relentlessly. Industry events flood advisors with dozens of new tools and ideas, but trying to implement everything leads to distraction. Instead, identify one to three ideas that meaningfully improve your firm and focus on executing those relentlessly throughout the year. 
“Relentless” improvement is more about mindset than technology. The real takeaway from Orion Ascent wasn’t just AI or new fintech announcements—it was the mindset of continuous improvement. Firms that consistently ask how they can serve clients better, improve workflows, and elevate their teams are the ones that ultimately win. 
Quotes
“Relentless means find a theme, find a thing that matters that you can relentlessly pursue.” ~ Jessica Perez
“If you are not actively in play right now, thinking about how your firm can handle AI to serve your clients, you're gonna have a lot of problems.” ~ Jessica Perez
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