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Finding What’s Next: How Values and Vulnerability Drive Career Pivots with Jake Gunn-Sandell
Episode 7 Jake Gunn-Sandell
On this episode, I speak with Jake Gunn-Sandell, Director of Strategic Affairs at Instructure (the company behind Canvas), about his incredible journey. We discussed his bold career pivots, particularly his high-stakes transition into executive search, where he developed the innovative 'Polymath Practice'—a powerful framework for C-Suite recruiting.
I learned so much about how Jake leveraged vulnerability and strategic networking to make the leap from placing top talent to a pivotal leadership role in Education Technology (EdTech). I think this conversation offers a powerful blueprint for successful job searching and personal growth, emphasizing the need to ask critical questions, identify one's values, and remain adaptable throughout major career changes.
💡 Actionable Takeaways I Learned from Jake- Embrace Vulnerability for Professional Growth: Ask probing questions, and let intellectual curiosity guide learning. This builds trust and accelerates skill acquisition.
- The Polymath Practice: Jake's strategy to compartmentalize new, complex roles into simple, core subjects (e.g., Psychology, Tech, Finance) to make major career pivots manageable.
- Strategic Networking is Essential for Job Searching: Focus networking efforts on leaders and companies you admire. Finding the right organizational culture is as important as the role itself.
- Establish Credibility, Sell the Dream, and Slow Down: These three steps are what Jake found critical for building influence and trust in any leadership position or high-stakes environment like executive search.
- Identify Your Values and Goals: Jake defined his next move by writing down what he wanted (lead more, travel more, give back). A clear personal vision for guiding career pivots is essential.
- Creative Thinking Unlocks Opportunity: Challenge assumptions about the "perfect" candidate or the "obvious" career move. Leverage transferable skills to pivot into new sectors like EdTech seamlessly.
Chapters
00:00 Introduction and Background
03:30 Career Pivots and Challenges
13:35 Using Vulnerability in Executive Search
20:52 Fundraising Challenges in Nonprofit Work
22:54 Embracing Vulnerability in Leadership
24:34 Navigating Career Transitions SPMB to Instructure
30:03 Identifying Personal Values and the Impact of a Career Coach
32:05 Leveraging Relationships for Career Growth
34:47 Strategic Job Searching
38:34 Understanding Your Identity as a Builder
Guest
Jake Gunn-Sandell’s career is a masterclass in the power of the career pivot. He currently serves as the Director of Strategic Affairs at Instructure, helping define the future of education through his work in government affairs and strategic partnerships. Before moving into EdTech, Jake excelled in the demanding world of executive search, where he built the Polymath Practice—leveraging transferable skills to place C-suite leaders across every major tech vertical. From the fast-paced environment of recruiting top executives to his early days as a Disney character performer, Jake attributes his success to embracing vulnerability, strategic networking, and a relentless drive for personal growth. He remains committed to his community as a board member for the Arapahoe Rescue Patrol.
LinkedIn: https://www.linkedin.com/in/education-the-first-step/
Host
Kelly Dwyer is an executive coach and facilitator. Through her podcast Life from Within, she opens up real conversations about personal growth, career crossroads, and the inner work of leadership. She created the show to explore the moments of courage and clarity that spark inner shifts and lead to meaningful outer progress. In her coaching and facilitation work, Kelly helps leaders uncover what matters most to them, navigate inflection points with intention, and build the kind of impact that grows from the inside out.
Coaching and facilitation: https://kellydwyer.co
Resources mentioned
- Jake on LinkedIn - /in/education-the-first-step/
- Arapahoe Search and Rescue - https://www.arapahoerescue.org/
Listen and subscribe
Apple Podcasts | Spotify | YouTube
Follow Kelly
Instagram – @kd_lifefromwithin
LinkedIn – /in/kellydwyer
Sign up for updates
View all episodes
By Kelly DwyerEpisode 7 Jake Gunn-Sandell
On this episode, I speak with Jake Gunn-Sandell, Director of Strategic Affairs at Instructure (the company behind Canvas), about his incredible journey. We discussed his bold career pivots, particularly his high-stakes transition into executive search, where he developed the innovative 'Polymath Practice'—a powerful framework for C-Suite recruiting.
I learned so much about how Jake leveraged vulnerability and strategic networking to make the leap from placing top talent to a pivotal leadership role in Education Technology (EdTech). I think this conversation offers a powerful blueprint for successful job searching and personal growth, emphasizing the need to ask critical questions, identify one's values, and remain adaptable throughout major career changes.
💡 Actionable Takeaways I Learned from Jake- Embrace Vulnerability for Professional Growth: Ask probing questions, and let intellectual curiosity guide learning. This builds trust and accelerates skill acquisition.
- The Polymath Practice: Jake's strategy to compartmentalize new, complex roles into simple, core subjects (e.g., Psychology, Tech, Finance) to make major career pivots manageable.
- Strategic Networking is Essential for Job Searching: Focus networking efforts on leaders and companies you admire. Finding the right organizational culture is as important as the role itself.
- Establish Credibility, Sell the Dream, and Slow Down: These three steps are what Jake found critical for building influence and trust in any leadership position or high-stakes environment like executive search.
- Identify Your Values and Goals: Jake defined his next move by writing down what he wanted (lead more, travel more, give back). A clear personal vision for guiding career pivots is essential.
- Creative Thinking Unlocks Opportunity: Challenge assumptions about the "perfect" candidate or the "obvious" career move. Leverage transferable skills to pivot into new sectors like EdTech seamlessly.
Chapters
00:00 Introduction and Background
03:30 Career Pivots and Challenges
13:35 Using Vulnerability in Executive Search
20:52 Fundraising Challenges in Nonprofit Work
22:54 Embracing Vulnerability in Leadership
24:34 Navigating Career Transitions SPMB to Instructure
30:03 Identifying Personal Values and the Impact of a Career Coach
32:05 Leveraging Relationships for Career Growth
34:47 Strategic Job Searching
38:34 Understanding Your Identity as a Builder
Guest
Jake Gunn-Sandell’s career is a masterclass in the power of the career pivot. He currently serves as the Director of Strategic Affairs at Instructure, helping define the future of education through his work in government affairs and strategic partnerships. Before moving into EdTech, Jake excelled in the demanding world of executive search, where he built the Polymath Practice—leveraging transferable skills to place C-suite leaders across every major tech vertical. From the fast-paced environment of recruiting top executives to his early days as a Disney character performer, Jake attributes his success to embracing vulnerability, strategic networking, and a relentless drive for personal growth. He remains committed to his community as a board member for the Arapahoe Rescue Patrol.
LinkedIn: https://www.linkedin.com/in/education-the-first-step/
Host
Kelly Dwyer is an executive coach and facilitator. Through her podcast Life from Within, she opens up real conversations about personal growth, career crossroads, and the inner work of leadership. She created the show to explore the moments of courage and clarity that spark inner shifts and lead to meaningful outer progress. In her coaching and facilitation work, Kelly helps leaders uncover what matters most to them, navigate inflection points with intention, and build the kind of impact that grows from the inside out.
Coaching and facilitation: https://kellydwyer.co
Resources mentioned
- Jake on LinkedIn - /in/education-the-first-step/
- Arapahoe Search and Rescue - https://www.arapahoerescue.org/
Listen and subscribe
Apple Podcasts | Spotify | YouTube
Follow Kelly
Instagram – @kd_lifefromwithin
LinkedIn – /in/kellydwyer
Sign up for updates