“Heather is an incredible wealth of knowledge, with the ability to navigate the practicalities of running a business while speaking to the core of what it means to be human. She helped us navigate a number of processes from hiring to values conversations, and always provided a grounded approach that was both pragmatic and effective.”
what we solve
Your startup is scaling fast. You need to scale, too.
We know the feeling because we’ve been there. Your company is growing more complex. Every day feels like the biggest job of your life.
You wake up knowing that what worked last month won't work this month. The systems that got you here are breaking. The team that was perfect at 25 people is struggling at 100, and you wonder how you'll continue to scale your team and yourself.
You're moving fast, and sometimes it feels like you're barely keeping up with the company you helped build.
Enter Waypoint Works:
We guide founders and emerging leaders with coaching, expert advice, and workshops that scale with their business.
Let us help you thrive at the speed of your startup’s success.
Coaching | Embedded Advisory | Workshops | Offsites

The High Slope Opportunity
High Slope Talent are the unproven, high potential hires that may even start lower than most hires on day one, but their capabilities scale with business growth over time.
Waypoint Works turns hires into leaders who keep pace.
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Dr. Heather Doshay
Founder
about
More than a coach and a consultant. You’ve got someone on your side.
Dr. Heather Doshay is the Founder of Waypoint Works, a coaching and embedded advisory partner helping startups scale intelligently with High Slope Talent. Previously a Partner & Head of Talent at SignalFire and the founding executive and VP of People at Webflow, she brings hard-earned operator insights to founders and their teams. She holds a doctorate in Organizational Leadership, a Masters in Adult Learning, and her insights have been featured in The Wall Street Journal, The New York Times, and Forbes.
Services
From where you are to what’s next
We provide a flexible and customized suite of services that enable your most important asset- your people. We’re deeply steeped in this ecosystem, so if we don’t provide it, we’ll intro you to who does it best.
Testimonials
Trusted at pivotal moments
“Most leaders struggle to grow quickly enough to keep pace with their company’s growth, but with a coach like Heather, you have the opportunity to scale your skills and successfully navigate each stage of the company’s journey. She helped me see things from a new light and in moments where it felt like the earth was opening up and eating me, she helped put it all together!”
“I have found Heather's approach to coaching as a refreshing and agile style that enabled me to drive what I needed most each session, holding a deep connectedness with my long-term vision while receiving her personal wisdom & professional frameworks. I felt like I could bring anything to our sessions together and walk away with more confidence and more clarity on what was ahead for me.”
“Heather was instrumental in helping ensure we started Peer AI with the right foundation. She advised us across the board, on topics including cultural aspects (how to structure our first offsites, process for defining and aligning on values, creating fit-for-purpose rituals to ensure adherence to our values) as well as more tactical (structuring appropriate compensation packages, defining titles and employee bands, creating our first parental leave policies). As our company has grown, Heather has ensured we put the proper measures in place to scale -- including how to think about compensation, performance management processes, and org structure. As a first time founder, this wealth of knowledge applied specifically to our situation was incredible -- I am grateful to have had Heather's guidance!”
“When I started working with Heather, she had just left SignalFire to build her own thing. And I knew I wanted to work with her immediately. I had this dream to put on a VC Summit that brought the best Talent Partners at top Venture Firms together for a day of programming and connection. And while I had relationships in the VC ecosystem, Heather had been on the inside and was a magnet. Heather advised on the guest list, content, and put together a workshop that ended up being one of the most successful parts of the day.
In addition to being whip smart and a joy to work with, Heather is also incredibly fast. I can't overstate how important that trait is in a third party partner.”
“I began working with Heather when I joined an executive team for the first time, following the departure of my department's leader. Heather has been an incredible influence on my career growth and on my ability to quickly adapt to the needs of my new position. She's helped me recognize my strengths, taught me how they apply in an executive context, and helped me tremendously in shifting from functional leadership to business leadership.”
“Heather has been an incredible coach and a true asset to have in my corner. She has helped me navigate numerous challenges at work with a level of clarity, thoughtfulness, and ease that I genuinely value.
One of Heather’s greatest strengths is her ability to communicate complex ideas in a way that feels clear and approachable. She brings practical frameworks, examples, and strategies into our conversations that help me step back from a situation, see it differently, and figure out how I want to move forward. She has a way of making you feel less alone in whatever challenge you’re facing.”
“I've had the opportunity to work with Heather in two capacities. First, as a new people manager navigating the everyday work of supporting a teammate's growth and success. Heather's deep knowledge of people management helped me better understand my role and responsibilities as a manager, and gave me frameworks and mental models for shaping my approach to supporting my direct reports.
I've also received individual coaching from Heather, who guided me in designing a right-sized approach to performance goal setting, drawing on her expertise in performance management and development. She also supported me in building and implementing a change management plan for rolling out a new system — one that was very positively received across staff. Throughout our coaching, I felt how much care and thought Heather put into understanding my specific challenges, and I'm deeply grateful for the attention she gave to helping me grow.”
“Working with Heather has made me a better leader and business partner. Going into executive coaching, I wasn't entirely sure where my business could (or should) be headed, and what exactly my part was to play. Heather helped me identify what's most important to me in my growth, and gave me the confidence to hold onto that north star whenever the business was rocked by waves. She took many of my assumptions and repackaged them in a way that made me question the story I was telling myself, ultimately allowing me to find new perspectives. As a result, I feel more self-assured in my role as COO, in our business goals, and in the future of Great Team Partners.”
“Heather is an exceptional coach. What impressed me most was how quickly she was able to cut through the noise and help me see my own experience more clearly. She has a superpower for asking the right questions at the right time, helping you uncover insights that were already there but hard to articulate on your own. At the same time, she brings deep practical experience, so when she offers perspective or advice, it is thoughtful, grounded, and immediately useful.
I left our conversation feeling clear-eyed about how to approach the next chapter of my career. Heather helped me reconnect with my strengths and reframe my thinking in a way that made the path forward feel less overwhelming. If you’re navigating a transition or trying to think through what comes next, she’s the kind of coach who helps you find clarity and trust your own direction.
If you’re not sure whether you need a therapist, a career coach, or a life coach… you probably just need Heather.”
Blog
Ideas to guide what’s next.
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16 Aug 2025
Waypoint original
Why Waypoint Exists: A Love Letter to Startups
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23 JAN 2025
Our thoughts in the wild
Mastering The 9-Box Talent Review: A Guide for HR Professionals (republished from People Managing People)

9 OCT 2018
our thoughts in the wild
The Types of Team Members You Need to Hire at Each Stage of Your Business (republished from Entrepreneur)
Ready to climb?
©2025
Go Farther, Together

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