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E60 - "Sales is a Lifestyle, Not Just a Career."

With Jesse Woodbury, Founder of Sales Players

Oct 22, 2024

Hitesh and Jesse Woodbury, co-founder of Sales Players, discussed their experiences in the tech software startup industry, with a focus on the challenges faced by individual contributors and the importance of building a strong business case.

They also discussed the importance of self-enablement and personal development in sales, the value of seeking mentorship and in-person opportunities for growth, and the trade-offs between salary and equity in the SaaS industry.

Lastly, they touched on the topic of building one's own brand, with Jesse sharing his journey into content creation and emphasising the importance of authenticity and persistence.

  1. "How Enterprise Sales Changed Over a Decade" (03:04)
    Jesse highlights the shift in decision-making for Enterprise sales, with more deals requiring CEO or CFO involvement, reflecting a more cautious market landscape.

  2. "Build the Business Case from Day One" (06:01)
    Jesse advises sales reps to focus on how their product saves money, makes money, or reduces risk, emphasizing the importance of connecting these points to CEO and CFO priorities.

  3. "Navigating Proof of Concept Requests" (10:00)
    Jesse shares how to turn proof of concept requests into opportunities by structuring them as paid trials that roll into longer-term agreements.

  4. "Sales: A Lifestyle, Not Just a Career" (22:02)
    Jesse explains that successful selling requires treating sales as a lifestyle, dedicating time to self-education, content creation, and relationship-building.

  5. "From Listener to Podcast Co-Host" (28:35)
    Jesse recounts how a LinkedIn message from a fan turned into a partnership, with that listener eventually becoming his podcast co-host.

  6. "The Equity vs. Base Salary Debate" (31:05)
    Jesse cautions against prioritizing equity in startup roles, advocating for a focus on higher base pay and achievable commission opportunities.

  7. "Investing in Yourself Pays Dividends" (26:23)
    Jesse emphasizes the value of investing personal resources, like attending conferences or pursuing learning opportunities, to accelerate career growth.

  8. "How to Build Your Personal Brand Authentically" (37:03)
    Jesse advises aspiring content creators to start with their unique stories and focus on authenticity, treating it like a personal journal rather than chasing trends.

  9. "The Power of In-Person Collaboration" (18:49)
    Jesse reflects on the invaluable insights gained from working in-office alongside founders and attending on-site customer meetings.

  10. "Favorite Career Memory: The Startup Office Energy" (43:30)
    Jesse recalls his most impactful career experience: being part of a high-energy startup environment where learning and collaboration were constant.

  1. "How Enterprise Sales Changed Over a Decade" (03:04)
    Jesse highlights the shift in decision-making for Enterprise sales, with more deals requiring CEO or CFO involvement, reflecting a more cautious market landscape.

  2. "Build the Business Case from Day One" (06:01)
    Jesse advises sales reps to focus on how their product saves money, makes money, or reduces risk, emphasizing the importance of connecting these points to CEO and CFO priorities.

  3. "Navigating Proof of Concept Requests" (10:00)
    Jesse shares how to turn proof of concept requests into opportunities by structuring them as paid trials that roll into longer-term agreements.

  4. "Sales: A Lifestyle, Not Just a Career" (22:02)
    Jesse explains that successful selling requires treating sales as a lifestyle, dedicating time to self-education, content creation, and relationship-building.

  5. "From Listener to Podcast Co-Host" (28:35)
    Jesse recounts how a LinkedIn message from a fan turned into a partnership, with that listener eventually becoming his podcast co-host.

  6. "The Equity vs. Base Salary Debate" (31:05)
    Jesse cautions against prioritizing equity in startup roles, advocating for a focus on higher base pay and achievable commission opportunities.

  7. "Investing in Yourself Pays Dividends" (26:23)
    Jesse emphasizes the value of investing personal resources, like attending conferences or pursuing learning opportunities, to accelerate career growth.

  8. "How to Build Your Personal Brand Authentically" (37:03)
    Jesse advises aspiring content creators to start with their unique stories and focus on authenticity, treating it like a personal journal rather than chasing trends.

  9. "The Power of In-Person Collaboration" (18:49)
    Jesse reflects on the invaluable insights gained from working in-office alongside founders and attending on-site customer meetings.

  10. "Favorite Career Memory: The Startup Office Energy" (43:30)
    Jesse recalls his most impactful career experience: being part of a high-energy startup environment where learning and collaboration were constant.