The first time I met Alex Lin, he floored me.

It was late 2016, when I received an SDR style outbound email sequence from Alex explaining why my then company, Rainforest QA, should hire him. It was well-researched and persistent as if this was what he had been doing for decades. He was excellent at prospecting.

As a people and talent leader, I have seen it all. I once had a candidate mail me a physical shoe to "get a foot in the door." I have had clever cover letters and elaborate video pitches. I had never had someone model the role itself as a way to show versus tell what they could do. He grabbed my attention; I was impressed. But nothing impressed me as much as what his resume revealed:

Alex had no sales experience. No tech experience. He had never even worked an office job.

Alex was a firefighter and paramedic sitting on what people in the fire service call "the golden ticket." Get the job, work it for 30 years, retire with a pension by 52 years old.

He met the team, continued to impress, and we hired him.

I did not know it then, but Alex and I were both making a high risk bet on each other. Mine was on a non-traditional candidate without the typical experience set. His bet was leaving the safety of a 30-year pension path for income potential with no floor and no ceiling. 

Within a quarter, Alex was the standout number one SDR on the team. He consistently topped all dashboards in Salesforce, both activity metrics and outcomes. He was promoted to Account Executive in under a year, and when he beat his annual quota in well under a year, was promoted again to take on bigger and bigger accounts.

When one of his mentors at Rainforest accepted a role as the first sales manager at Gong, Alex followed him as his first account executive hire. Alex helped take Gong from roughly $6 million in revenue to over $250 million in revenue in under six years. Today, he’s a Strategic Account Executive at Tailscale, partnering with some of the world’s largest enterprises while building a life that once felt far out of reach. He lives in Hawaii with his wife and new baby, deeply grateful for the opportunities his career has created  -  but at his core, he still carries the same drive, humility, and determination he had at 22 when he first joined the fire service.

His story alone is High Slope screaming at the top of its lungs, but what’s even more inspiring is the lessons he’s learned along the way. 

PEAKS and Valleys

When we talk about High Slope at Waypoint Works, we’re talking about people who are bursting at the seams with PEAKS traits. Alex points to three of them as his core: persistence, action orientation, and knowledge sponge. He lovingly referred to it as PAK. With Alex, PAK is so robust, that even if at times he’s acknowledged limits with emotional grounding, it’s never held him back from achieving what would be impossible for most.

"If I want something, I will be persistent in achieving it," he explains. "And I am not someone that will sit back and see how things go. I get impatient, for better or worse, and I just go for it."

The knowledge sponge piece is where he has had to be more deliberate. What started as raw curiosity has turned into a discipline. When something catches his interest, he has a process: First, he asks himself if the topic gives him real energy. If the answer is yes, he goes deep. YouTube, podcasts, articles, books, and most importantly, conversations with people already in the space. He will “listen to every interview the founders are on to learn more about them and their vision”.

After six years at Gong, he took a well-deserved sabbatical with no job lined up. However, within weeks, he realized he could not handle being someone who didn't work. So he started learning instead. He picked apart AI, computing infrastructure, and the data layer. He cold-emailed founders and CEOs of companies he had never used and asked for time. 

"The ones that gave me time, I still remember them," he says. "The ones that did not, I remember those too."

Emotional grounding is the most challenging trait for many High Slope people – it finds friction up against the other, often more dominant traits like persistence and action orientation. Patience can feel like not getting things done, and that means it’s critical for High Slope Talent to see the possibility and the learning opportunity ahead to stay focused.

How to Spot High Slope Talent

Most founders and sales leaders will agree they want to recruit as many people like Alex Lin as possible. Yet they almost exclusively pass on them as too risky and instead narrow their pipeline to a handful of pedigreed companies who seem like safer bets. Pattern matching to pedigree is an easy mental shortcut, and in a sea of founder decisions, this is a too-often missed opportunity.

"A lot of companies have missed really good hires because of that mindset," Alex says. "They are not hiring based on how someone has succeeded in the version of life they have had."

The intangibles that best predict who will figure it out and adapt to a changing context, the things that made Alex an instant top SDR with zero tech experience, are the things most processes screen out. They’re asking for 4+ years relevant experience at companies like X and Y, without paying heed to the underlying capabilities that led to any type of success.

With AI reshaping what "experience" even means at work, screening for slope over pedigree has never mattered more. Companies are wise to consider how candidates adapt to new contexts.  To consider how career changers actually have the hidden edge in this new environment. They’re proven entities when it comes to reinventing how work gets done.

Alex offers a simple rubric. He calls it “the basics”:

• Are they a good human?
• Are they highly curious and driven by what they learn?
• Are they self-aware and coachable?

Job-specific skills are trainable. These traits are not.

"I put way more energy into the person who is genuinely curious, motivated, and a good human than the person with the high pedigree," he says. "I have seen way more people with great resumes flame out than people with all the other things."

Most leaders nod along to this in theory, and few make hiring decisions this way. If you want High Slope Talent in your pipeline, your interview loop has to detect PEAKS in motion. That means behavioral interviews that test how someone handled real obstacles, even in a different context. It means letting candidates show, not tell. If you pay close attention, the signals are everywhere. Watch how they research and prepare for the interview itself.  Recognize the potential when you see an email that looks like an outbound sequence sent by a firefighter applying to his first SDR job.

And if you are the candidate getting passed over, borrow Alex's reframe:

"When people say no to me, I think, oh, that is the wrong decision. Watch me be successful, or watch me help someone else be successful who gave me the shot."

Alex’s advice is easy to understand and hard to do: treat rejection as information about the other party, not a verdict on you. To take a note out of Steve Martin’s playbook and “be so good they can’t ignore you”.

How to Grow and Retain High Slope Talent

When Alex left Gong, it came from a growing realization that he was no longer being stretched in the ways that mattered most to him. The work had become familiar and predictable, and while that brought comfort, it also meant fewer opportunities to learn and grow. He has always believed in the balance of “earning and learning,” and over time, he felt the learning side of that equation beginning to fade.

“I realized I wasn’t pushing myself anymore,” he says. “The challenges that once excited me had become routine. For me, growth comes from stepping into the unknown and feeling a little uncomfortable. That’s where the real learning happens.”

Companies need to paint an exciting picture for its top-performing talent, a picture that keeps them motivated and focused.  The good news is that this costs nothing, if you have the enabled managers in place who can guide talent to opportunity within companies as well as you did when you attracted the hire to join in the first place.

Alex reflects on his best manager, who was able to motivate him and grow his slope the most: Justin Geller, first his mentor at Rainforest and later his first manager at Gong. When Alex was an SDR pestering AEs to learn their job, Alex jokes that most of them probably found it annoying. Justin was different. He spent real time with Alex, patiently explaining things to him. He told Alex what was working and what was not, in a way Alex could act on the same day. He knew what gave Alex energy, which is why Alex was the first call when Justin moved to Gong.

Great managers see High Slope Talent for what it is, and they customize their approach to unlock what’s possible. When I asked what stood out most about Justin, it was this:

"I trusted him with my career," Alex says. "I knew his intentions. I knew he had what was best for me in mind."

The worst managers in his career did the opposite.  He explains he “ realized that the managers [he] struggled with most were those who focused more on appearances than execution, which sometimes undermined the sense that we were all on the same team.”

This is unfortunately common, and talent is squandered when it happens. Too many good performers get promoted into management and see their direct reports of success as their competition versus an asset. The best companies help managers understand that they win when their team wins, and “pestering” is a version of motivation bursting at the seams, needing guidance and scope to solve the next challenge ahead. This is an opportunity, not a problem if you can harness it. Suffocate their curiosity, and they will burn out and leave.

He shared that his decision was driven less by the company itself and more by a personal sense of stagnation in his role over time. While he continued to value the team, culture, and opportunity overall, he felt he had moved beyond the stage of growth that energizes him most, specifically the early-building phase where he could help define strategy, identify repeatable processes, and create scalable motions from the ground up. Alex is most motivated when operating in environments that require experimentation, problem-solving, and building something repeatable that can materially shape the business.

What has always driven him is the balance of “learning and earning”: being challenged to grow, push into new territory, and raise the bar on what’s possible as an individual contributor. He noted that if there had been a clearer path toward owning and building around a small number of highly transformational “dream accounts,” with the right support, strategic investment, and long-term upside attached to that mission, it likely would have given him a compelling reason to stay longer. That type of opportunity, where he could both pioneer new approaches and operate at a highly strategic level, aligns most closely with the kind of work that keeps him deeply engaged and motivated over the long term.

At Waypoint Works, we call this archetype “deep sea divers”, and most companies only optimize for “climbers”. Companies should consider what internal mobility looks like for all types of career growth, and managers should be clear on the employee’s “why” and have a candid, ongoing conversation about what “path” each top performing employee is optimally on–retention might be an easier solution than you think. 

If Alex Built the Company

I asked Alex what he would do as a founder, what kind of culture he would build. His take was both timely and timeless:

Talent is P0. “In a world where AI is eroding traditional technical moats, a company's real competitive edge is the people inside it.” Alex believes any leader who treats it as a downstream or administrative function is going to be outbuilt by leaders who treat it as their personal priority number one.

Align everyone on the collective outcome. "You will be surprised how many companies do not do this," he says. "There is so much internal misalignment and so much goal sprawl." Pick the goal, make sure every team's work ladders up to it, and reset if you have to.

Hire for trajectory, not pedigree. "The best people I have seen are the ones who had to reinvent themselves," he says. “Curiosity, grit, speed of learning, self-awareness, and coachability beat brand names every time.”

Build a culture where people fix the problem they see. "Companies say they let people fail fast and learn. Most do not actually do it. Make the meritocracy real. If you see the hole, you have permission to fill it. Earn your role by fixing what is broken in front of you.”

Design career paths for deep specialists, not just future managers. Alex has always felt most energized as an individual contributor, where he can stay close to the work, tackle complex challenges, and create outsized impact. For him, compensation has never been purely about money — it’s been a reflection of the value created for customers and the business. He believes companies can unlock tremendous potential by building IC paths that offer the same level of growth, challenge, recognition, and long-term opportunity traditionally associated with management tracks. The best environments create space for people to continue “learning and earning” without feeling like leadership is the only path to advancement.

Reward people who do what others will not. Alex attributes a lot of his success from a willingness to do the work others did not raise their hand for. That deep ownership coupled with low ego would be rewarded in his company.

Advice for Emerging Talent

Alex looks back at his decision to change his career with utter gratitude. That job change made his current life possible. While it was riskier, it helped him find financial freedom much younger than a pension would allow, he met his wife at Rainforest, and he grew and evolved his life’s why. Here’s what he wants emerging High Slope Talent to know if they are plotting their own path:

Everyone faces some level of impostor syndrome. "I honestly feel like an impostor a lot of the time, even though people read me as confident," he says. "Confident-sounding people question themselves too. Do not assume otherwise. Especially managers." Remember that on the inside, everyone is still figuring it out.

Do not be the smartest person in the room. If you are, you are not going to learn anything. Find the room where you are slightly out of your depth and grow into it. Find the people you can trust and learn from. 

Reinvent yourself on purpose. The best people he knows have all done it at least once. The willingness to be a beginner again is a slope multiplier, an accelerant to growth. 

Reverse-engineer your life. Start with the bigger questions: What kind of life do I want to build? Who do I want to become? Then work backward into the career, environment, and opportunities that help you get there. Your “why” can evolve over time, but it should remain your north star.

For Alex, that “why” is much clearer today than it was earlier in his career.

“The existential angst I always had is gone,” he says. “My motivation now is centered around providing for my family and creating opportunities and experiences that I never had growing up.”

Raised by immigrant parents, many of the things he experiences today once felt completely out of reach. The kid sitting in a fire station modeling out an SDR role just to get a foot in the door now lives in a valley in Hawaii with his wife and new baby, surrounded by mountains with the ocean outside his window. For him, “learning and earning” was never just about career progression - it became the vehicle to build a life, create stability for his family, and experience a world he once only imagined from a distance.

‍