Leland Holcomb
Senior Innovation Associate at CSAA Insurance Group
Greater Hartford
Overview
Work Experience
Senior Innovation Associate
2022 - Current
Helps design and deliver AI-powered claims products, developing product requirements, business cases, and executing pilots. Drives adoption strategies, stakeholder alignment, and enterprise rollout of solutions with projected $10M–$30M in savings. Conducts vendor and market analysis on emerging market trends (ex: AI, EVs) to inform strategy.
CSAA Insurance Group is an insurance company that offers automobile and other personal lines of insurance to AAA members.
Adjunct Instructor - NSF I-Corps Hub Northeast (current)
2020
Advises student-led ventures on business model design, customer discovery, and MVP development. Co-teaches venture development courses aligned with NSF I-Corps methodology, supporting over 300 entrepreneurs from ideation through early validation. Adjunct Professor - Insurtech Experiential Course (2021-2023): Adjunct professor for an experiential insurtech course where students supported real startups in addressing growth challenges. Oversaw team-based consulting projects with host companies, focusing on strategy, business modeling, and customer discovery.
Director Of Business Development (Technology)
2021 - 2022
Led technology sector growth strategy for the state of Connecticut. Managed company recruitment, conducted due diligence, and served on the state blockchain task force to inform tech policy.
AdvanceCT strives to build a place where business, government, higher education and nonprofits come together.
Co-Founder
2017 - 2022
Built searchable music sync licensing tool; drove 5.3M+ impressions and 67K users.
Customer Success Manager
2020 - 2021
Managed delivery and iteration of an AI analytics platform for insurance agents. Directed a 20+ person team through feedback-driven product updates, scaling the platform from 2 to 60 users with 0% churn. Led onboarding, rollout, and customer success operations.
Head of Scouting & Investor Relations - Hartford InsurTech Hub
2018 - 2020
Sourced and evaluated over 4,500 insurtech and digital health startups. Selected 21 ventures for acceleration, supported 25+ startup financings, and led investor engagement. Organized global pitch events and connected startups to enterprise and capital partners.
Global Fellow - Impact Investment
2017 - 2017
Conducted due diligence, financial modeling, and impact assessments for investments targeting underserved populations in India. Supported investment decisions across social enterprises delivering both financial and measurable social returns. Strategic consultant (e.g. functional redesign, growth strategy, and BP design) to regional portfolio company.
Legal Assistant
2015 - 2016
Supported litigation and business law practice through case file organization, trial prep, legal research, and operational support for business development activities.
Project Coordinator - Workforce & Public Policy
2014 - 2015
Developed initiatives to support business growth and workforce development. Led research and reporting on economic indicators and secured funding for local minority-owned business programs.
Admissions Fellow
2011 - 2014
Interviewed prospective students, evaluated applicants, and represented the college in campus tours and outreach efforts. Served as a trusted voice in admissions decisions.