Jaymie didn't interview for her job at Dscout. 

There wasn't a job opening at the then ten-person startup. She'd had an informational coffee with someone and left energized by their work in user research. When she asked if they had open roles, she was met with a “not at this time”. Most people would have sent a thank-you email and moved on.

But High Slope Talent doesn't stop at no.

Jaymie went home and read up on everything she could find about Dscout. Three pages deep on Google’s search results on the company, she found an unlisted job description that loosely fit her background. She rewrote it for what she thought they should hire for. Then she created an eight-page cover letter, designed it in Dscout's brand, had it professionally printed and bound like a book, and dropped it off at reception that Friday.

High Slope Talent isn’t just persistent and action-oriented, they floor you with the lengths they go to achieve their goals.

Monday morning, Jaymie received an email: Come in and talk to the CEO Michael about whatever job you want here.

That was eleven years ago. Today, Dscout has grown to nearly 200 employees, and Jaymie has grown into the role of VP, Operations for the company. Over her High Slope journey, she practically reinvented her role every six months, built and led a team of 60+, and navigated the classic startup evolution from scrappy chaos to structured scale—all without leaving the company.

What High Slope Talent Looks Like

At Waypoint Works, we study what we call "high slope" talent: people whose rate of learning and impact accelerates faster than their peers. We've identified five traits that characterize these leaders: Persistence, emotional grounding, action-orientation, knowledge sponge, and systems thinking (PEAKS).

But Jaymie's story reveals something the framework alone can't capture: how these traits compound in practice, and how the right company environment can amplify them.

“If you keep showing up with high-quality work and focus on making things a little bit better for the people around you, they start to trust you,” Jaymie says. “That trust is what pulls you into the tricky, high-stakes projects that shape a company. That’s your seat at the table.”

This is the flywheel that High Slope Talent embraces. Jaymie described two categories of attributes that have been the keys to her success:

1. The internal category: intrinsic motivation, high standards, deep organization
2. The external category: directness, low ego, dependability

Together, they force multiply to build trust. And high trust allowed Jaymie to be invited to the table over time.

The Action-to-Systems Evolution

Early in her tenure at Dscout, action orientation was Jaymie's unlock. By the age of 24, she had led all-day training sessions for dozens of people at Fortune 500 companies. By 25, she was trusted to manage a team. By 30, she'd hired and built a 50-person organization.

"I had a six-month half-life at Dscout," she says, quoting her former manager and company CEO Michael. "My job changed just as fast as the company was changing." 

But as Dscout matured, Jaymie noticed something critical: the action orientation that made her invaluable early on needed a counterweight. "As you get to a more complex organization, you can find yourself running into a wall or making changes that don't stick," she reflects. Systems thinking is the critical counterpart to action orientation as a company matures, because actions alone at a scaling company are chaotic for everyone else involved.

This evolution separates high slope people who plateau from those who continue accelerating. Many early-stage operators can't make the leap to strategic, systems-thinking. Others become strategic but lose their ability to execute. Jaymie maintained both: “the person who can see the mountaintop and chart the path, and also grab the machete and start cutting through the brush”.

The Uncomfortable Truth About Growth

"Growth feels like incompetence," Jaymie explains. 

It's the most honest thing anyone said to me about high slope development, and in hindsight I see it everywhere. High Slope Talent isn’t immune to Impostor Syndrome. Jaymie hasn’t felt totally ready for every new role she's taken on. The difference between her and others? She doesn't let that feeling paralyze her. She seeks out the discomfort.

According to Jaymie, the solution isn't confidence. It's action. "Just keep one foot in front of the other. The stakes are higher, but the game is still the same. You keep trying, you keep learning." 

This is especially crucial as companies mature and bring in external executives with proven expertise. Jaymie has watched peers exit as new leaders arrive, and felt the creeping concern about the Peter Principle: being promoted to a level of incompetence. Her response wasn't to protect her territory. It was to embrace the new expertise of external talent while owning the complimentary value she brings as high slope internal talent. “New voices present another opportunity to learn."

How Dscout Cultivates Slope Amongst Employees

High slope people need the right conditions to thrive. Dscout provides three critical elements:

1. Internal mobility as a norm. Jaymie could see the possibility of lateral movement because it happened for others. When she lost her spark after ten years—maintaining the 60-person team she had built but rarely feeling outside her comfort zone—she pitched a new role in  operations leadership. The timing wasn't right. So she patiently waited eighteen months. "I had a history to trust him on that," she says of her CEO. He also gave her stretch projects to dip her toe into the work the new role would entail. Eventually, she moved into a new role that reignited her spark.
2. A transparent culture that welcomes critique. First, people need to have a clear understanding of the full business context, and then, people need to be invited to address issues head on. "It was okay to come forward with problems, especially when you had solutions," Jaymie notes. She manages Dscout's OKR program, where anyone can see anyone else's objectives in a shared database. "It's really interesting to see who turns that knowledge into power," she observes. "That's a really good clue as to who might be a high slope person."
3. A manager who gives trust early and often. Michael, Dscout's CEO, never blocked Jaymie based on age, expertise, or title. He let her raise her hand to try things. After enough reps, she didn't have to raise her hand anymore—he started tapping her for tricky cross-functional projects.

Jaymie’s Advice

For founders hiring high slope talent: "Think really hard about when you need formal expertise and when you need someone who has agility and willingness to learn." Jaymie leans hard into challenge assignments that show how candidates show up and prepare with moments that floor you like she did in her cover letter. It’s more than a fancy resume.

For high slope people just starting out: "You can't push your way to a seat at the table. Focus on adding value. That doesn't mean always having the answer. Be a good listener, play back what you hear, highlight assumptions, bring the right voices and data together. People get stuck thinking 'I don't know the answer to that, so I shouldn't be solving that problem.' That's a lost rep."

And perhaps most importantly: "Your fresh eyes are golden." Jaymie tells every new hire this as she opens the invitation to share problems and solutions they see for the business. She takes it as a data point on someone’s slope whether or not they take her up on this. 

Jaymie’s Future Slope Story

Jaymie once worried that being a generalist was a liability. In a world that rewards specialization, where do problem-solvers fit at scale?

She's found her answer in the chaos of the AI era. "There's never been a better time to be a generalist," she reflects. "Being a really good thinker, connector, communicator…a lot of the things that would make someone high slope lend themselves to this topsy-turvy world of disruptive tech."

But more than AI alone, Jaymie’s generalist tendencies as a problem solver are what gives her optimism for the future. She's still at Dscout almost twelve years later with no plans to go anywhere soon. “Every time you deliver, you build trust. That trust creates new opportunities and each one keeps the flywheel spinning,” Jaymie says. “That’s what keeps me excited twelve years in — there’s always another challenge to earn.”

Emotional awareness and grounding are her signals, as she explains to me, "When I feel my slope start to flatten or I lose my spark, I'll know it's time for a new challenge because I've experienced that before." 

That's what real High Slope Talent looks like. Not a straight line up and to the right, but a person with PEAKS traits and the patience to reignite their own spark, over and over again.

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