I'm an entrepreneur and strategy executive working at the convergence of people, technology, and corporate development. My experience is in bridging main street and institutional capital in tech-enabled services: two buy-and-build platforms taken from relative infancy through institutional funding and beyond, less as an intermediary than as the operator responsible for the value creation thesis holding up after the check clears.
The largest obstacle to that value creation is business transformation. That is where my work concentrates, in three categories:
- Disentanglement of legacy organizations, processes, and technology stacks.
- Operating model design from first principles: systematized, technology-leveraged, able to absorb change, and built to give leadership the visibility it needs to operate institutionally.
- Corporate development architecture: the strategy and playbooks that let an organization source add-on opportunities, diligence them, and integrate them so the thesis survives contact with reality.
Underneath all three is a working philosophy built on influence and alignment rather than mandate. For founders, principals, and investors alike, the objective is usually the same: growth and institutional readiness without sacrificing the culture and durability of the business.
Recent work
Luxury residential design firm (Sep 2026 – present) — Operating advisor to a founder-led practice: restated economics, decomposed the business into a 180-task operating inventory to separate principal judgment from transferable process, and designing roles, pricing architecture, and the operating system (CRM, pipeline, project and procurement tracking). Work performed with AI leverage throughout.
Owner-led self-storage platform (July 2026 – present) — Group that builds, co-invests in, and manages self-storage facilities across five entities. Establishing the platform's first FP&A function: legacy disentanglement across the entity group, rebuilt data governance and reporting standards anchored on the existing ERP and CRM systems, and a dynamic financial model driving capital requirements and strategic decision logic. Work performed with applied AI throughout.
AI-powered audit automation platform (May 2026) — Advised the founder, a second-time YC-backed entrepreneur, on LATAM/US buy-and-build feasibility, roll-up economics, and the capital markets landscape.
Where I add the most value
- Pre-close investment readiness. Preparing owner-led businesses for institutional ownership: building the investment narrative, surfacing the value creation levers a sponsor will underwrite, and getting the operating foundation honest enough to survive diligence. Most often done as the internal company-side lead through the transaction itself.
- Disentangling legacy organizations. Most operating foundations were built for an earlier version of the business. The work is pulling apart the accumulated processes, roles, technology, and talent, then rebuilding in sequence: tasks before roles, roles before technology, technology before talent, talent before path.
- Designing operating models from first principles. Destination-state design of how the business runs end to end, with the process, systems, structure, and reporting leadership needs to operate institutionally.
- End-to-end M&A execution. Corporate development strategy through sourcing, underwriting, diligence, and integration. Integration is project-managed work, but it is also a relationship; most acquisitions lose their thesis quietly because only one of those was being run.
- Scoring talent against where the business is going. Evaluating people for destination roles rather than legacy ones, with learning velocity as its own axis. The institutional knowledge inside acquired companies is almost always worth more than the deal model suggests.
- Sequencing AI and systems leverage. AI is the train; the operating model is the tracks. Deciding what gets automated, what stays human, and what gets outsourced before adding headcount, not after.
How I engage
Project-based. Two scoped engagements I'm taking on this fall:
- Process-readiness sprint (4–6 weeks). For owner-led businesses 12–24 months from a recap or sale: a driver-based operating model, a current-state process map and charter, a reporting pack a sponsor's diligence team can work from, and a findings memo written the way they would write it.
- Interim integration lead (60–90 days). For sponsor-backed platforms with add-ons closed and no integration function: the integration playbook built and run against the next acquisition, then handed to the permanent hire.
Fractional executive. Embedded operating leadership (Chief Strategy Officer, COO, or chief-of-staff equivalent) on a part-time basis, for owner-led businesses preparing for institutional capital or platforms in the post-close stretch where a full-time hire is premature.
Advisory. Retainer-based and lower-touch: strategic counsel, deal review, organizational design, and hiring support for sponsors who want a consistent operator perspective across portfolio companies.
Board. Independent director or observer on sponsor-backed platforms.
I try to be direct about which mode fits. Sometimes that means saying you don't need me yet, or that you need someone else.
Experience
PE-backed insurance distribution platform (2020–2026) — Co-Founder and Board Member, then Chief Strategy Officer. Commercial P&C, personal lines, employee benefits, and payroll/HRO. Inc. 5000 honoree, 2025.
- Served as primary company representative and internal transaction lead through a 120-firm majority recapitalization process run by a national investment bank: built the investment narrative, identified and communicated the value creation levers, and drove institutional readiness ahead of closing.
- Acquired and integrated 27 owner-operated agencies, doubling enterprise scale in 2024. Created and executed the M&A and integration playbook, built the operating model greenfield, and managed all legal workstreams and external counsel coordination.
- Designed a stratified labor architecture combining onshore, offshore, and systems-enabled workflows that delivered meaningful payroll compression and revenue-per-employee expansion.
- Directed enterprise technology stack evaluation and rationalization (AMS, ERP, HRIS, CRM) and established the systems maturity roadmap and data governance foundation for institutional-grade reporting.
- Owned enterprise planning, board communications, and organizational design, translating sponsor objectives into coordinated execution across the leadership team.
Capital markets advisory practice (2020–2023) — Founder and Principal. Focused on operating businesses in alternative real estate; executed $300MM+ in transaction volume across self-storage, outdoor hospitality, and adjacent asset classes. Represented ownership in the sale of a 1MM+ sq. ft. self-storage portfolio to a publicly traded REIT, coordinating diligence across 14 ownership entities and the structural mechanics of a cash-consideration public REIT acquisition.
Vertically integrated self-storage investment platform (2018–2020; 2024) — Early hire (#3) and Acquisitions Lead during the platform's primary growth phase, scaling to 40+ properties; led investment execution including sourcing, underwriting, debt capital raising, and institutional investor relations. Returned in 2024 as Board Member to advise the vertical integration of an affiliated marketing services company, tenant insurance program, and proprietary PropTech platform.
Credentials
Certified Birkman Professional — Behavioral and occupational assessment, applied to organizational design, leadership development, and team structure.
BBA, Entrepreneurship — University of Houston, Wolff Center for Entrepreneurship. Led commercialization of Exostretch, a patented stretchable thin-film battery (NASA iTech, Caltech First Look West, Baylor New Venture).
Essays on business transformation and strategy are collected here as they're published. If you're weighing an engagement, or want to argue with something I've written, reach me at connect@rosssmolen.com.