Jos***ert

Founder, Principal

Education

Skills:

Start-up Ventures, Fundraising, Strategy, Publishing

Work Experience:

Founder, Principal at Walden

  • Location: Portland, Oregon, United States
  • Duration: 2024-07 to Present
  • Description: Leading Data, Research & Intelligence for the Outdoor Industry

Member Board of Trustees at Northwest Academy

  • Location: Portland, Oregon, United States
  • Duration: 2023-11 to Present
  • Description:

Owner / Investor at Alice

  • Location: Cincinnati, Ohio, United States
  • Duration: 2018-06 to Present
  • Description:

Chief Commercial Officer at Togo Group

  • Location:
  • Duration: 2019-09 to 2020-04
  • Description:

President & Chief Strategy Officer at Roadtrippers

  • Location: Sarasota, Florida Area
  • Duration: 2018-10 to 2020-04
  • Description:
AI Resume Analysis

Candidate Intelligence Report

AI-powered analysis from the perspective of a US hiring director — evaluating career continuity, growth trajectory, and role fit.

Career Continuity & Risk Assessment

Employment GapLow

No significant employment gaps are evident; the candidate has maintained activity across multiple ventures and roles since 2018.

Industry ConsistencyMedium

Experience spans startups, travel tech, media/advertising, and outdoor markets. While diverse, the core competencies align with tech-enabled consumer platforms and data-driven growth.

Tenure StabilityMedium

Several overlapping roles (Roadtrippers and Togo Group in 2019-2020) alongside long-running ventures suggest portfolio approach; this is not uncommon for founders but reduces perceived stability in traditional corporate paths.

Education-Career MatchMedium

Education details are not provided; assessment relies on extensive entrepreneurial and leadership experience, which mitigates but does not fully resolve educational alignment.

Career Growth Curve

Owner / Investor Lateral
Alice
2018-06 to Present
President & Chief Strategy Officer Entry
Roadtrippers
2018-10 to 2020-04
Chief Commercial Officer Lateral
Togo Group
2019-09 to 2020-04
Member Board of Trustees Lateral
Northwest Academy
2023-11 to Present
Founder, Principal Entry
Walden
2024-07 to Present
Assessment: Joshua demonstrates a consistent, growth-oriented trajectory anchored in founder-led initiatives, strategic leadership, and successful exits. The mix of scale-up leadership, board governance, and new venture creation suggests readiness for CEO, CSO, or growth-lead roles in fast-moving outdoor/travel tech businesses, or data-enabled platforms.

Best-Fit Roles (Top 5)

1

Chief Executive Officer - Outdoors Market Intelligence/Data Analytics Platform97% fit

Proven founder and operator with a track record of scaling tech-enabled ventures and leading data-driven product strategy in outdoor/travel spaces; strong fundraising and strategic leadership fit for a growth-stage, mission-driven platform.

2

Chief Growth Officer / Chief Commercial Officer - Outdoor / TravelTech Platform92% fit

Extensive experience with commercial strategy, partnerships, and revenue growth from Roadtrippers; capable of expanding market share and monetization in a global outdoors ecosystem.

3

President & Chief Strategy Officer - TravelTech Platform90% fit

Direct leadership in strategy and product development for a travel platform; aligns with overseeing cross-functional growth initiatives and corporate development at scale.

4

Chief Operating Officer - Outdoor / Conservation Tech Scale-Up86% fit

Operational leadership across multiple ventures demonstrates the ability to scale operations, align product and go-to-market, and drive efficiency in a fast-moving environment.

5

Head of Strategic Partnerships / Corporate Development - Outdoors / ArtsTech83% fit

Strong network across outdoors, arts, and media with deal-making and investment experience; suitable for leading strategic partnerships and corporate growth initiatives.

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