Taylor S. | Leland

Taylor S.

5.0

Studied at Harvard Business School

Works at Pathway Ventures

Available Monday at 4:00 PM UTC

Protected by the Leland Experience Guarantee

Available Monday at 4:00 PM UTC

Questions? Start chatting with this coach before you get started.

Interested in coaching?

Select a category below to view Taylor’s offerings.

Work Experience

Co-Founder, Co-CEO

Pathway Ventures

2020 - Present

Pathway Ventures is a pre-seed and seed stage venture capital fund investing in the human side of the future of work, which we define as startups driving new models of economic mobility.

Chief Operating Officer

FutureFit AI

2020 - 2024

FutureFit AI partners with Fortune 500 companies, governments, and workforce development organizations to provide workers with an AI-powered tool that acts as a "GPS for your Career". The platform uses advanced labor market data and equity-focused machine learning algorithms to identify an individual’s ‘starting point’ in the labor market, recommend best fit career path ‘destinations’, and build a personalized roadmap of learning, resources, and work opportunities to successfully guide them from point A to point B.

Venture Capital Fellow

Reach Capital

2019 - 2020

Led a market evaluation and thesis development of the middle skills pathways sector, speaking with industry CEO's and analyzing early stage investment opportunities in education and workforce development start-up's

Private Equity

Avathon Capital

2019 - 2019

➢ Led comprehensive market evaluation and thesis development in student financing sector, including deep dive on income share agreements (ISA's), speaking with industry CEO's to identify market trends and investable opportunities ➢ Supported all stages of investing lifecycle in the education sector, including sourcing, evaluation of new opportunities, due diligence on live deal, support of portfolio companies, and development of white paper

Chief of Staff

Nova Pioneer

2016 - 2018

Nova Pioneer is building a network of high-performing, low-cost schools across sub-Saharan Africa that prepare young people for success in the 21st century. As the Chief of Staff and a member of the Global Leadership Team, worked directly with the CEO and other Leadership Team members in achieving the organization's mission across the continent by spearheading cross-functional strategic projects that support the organization's top priorities. Sample project experience: ➢ Developed Nova Pioneer's internal communications strategy and rolled-out new communications initiatives for leadership communications, functional communications, and upward feedback to build clarity, culture, and shared ownership within the organization ➢ Developed Nova Pioneer's strategy around tracking and evaluating Key Performance Indicators (KPI's), including creating and rolling-out a KPI infrastructure and process that provided visibility to the organization's progress towards top priorities ➢ Created and executed the organization-wide fundraising initiative "Kilimanjaro 4 The Kids" which involved staff members (including me!) climbing Kilimanjaro to raise money for student scholarships and innovation programs, resulting in $30,000 raised and extensive press coverage across South Africa and Kenya ➢ Drove workstreams related to Nova Pioneer's capital raising process, including developing materials that articulated the organization's vision for impact and rationalized market value, which resulted in $20M in funding

Head of South America

Nova Pioneer

2015 - 2018

➢ Led marketing across South Africa, managing a team of 10, driving the strategic direction and managing to execution on how to build our brand across the region and hit enrollment targets across 5 schools ➢ Led overhaul of marketing function, re-building team (hiring 7 new team members), establishing team culture, and revamping ~75% of functional practices to optimize for efficiency and brand consistency