Hollis Mountain, LLC

Operations, Product and AI leadership for the hard parts of the climb.

Fractional CPO, COO, and generative AI enablement for distressed turnarounds, greenfield builds, and PE-backed portfolio companies. Thirty years of putting product and technology organizations on a faster path to measurable outcomes.

30+
Years building product and tech orgs
9
Companies where I owned product or operations
3
Companies I helped build that were later acquired
$1B+
Revenue platforms owned and operated
What I do

Senior operating leadership, available the way you actually need it.

I step into product and technology organizations that need to move faster, spend smarter, and ship outcomes that show up in the business. Fractional, embedded, or advisory.

01

Fractional CPO / COO

Executive product and operations leadership without the full-time line item. I run the org, set the strategy, and build the team that outlasts the engagement.

  • Greenfield product organization design
  • Turnaround and operational stabilization
  • Roadmap, P&L, and team scaling
  • Board and investor readiness
02

Generative AI Enablement

Production AI that moves real metrics, not demos. I help teams stand up practical stacks and ship features that change clinical, operational, and financial outcomes.

  • Claude API, Tool Use, Batch, and MCP
  • LangChain and data-to-insight pipelines
  • AI roadmap and capability building
  • Measurable-outcome framing for the board
03

Operating Partner / Advisory

For PE-backed portfolios and founders who need a seasoned operator in the room. Diligence support, value-creation plans, and hands-on help where it counts.

  • Portfolio product and tech diligence
  • Value-creation and 100-day plans
  • First-time CEO and founder mentorship
  • Chief-of-staff-level execution support
How I work

Walk in. Stabilize. Build the thing that lasts.

The pattern is consistent across every environment I have entered, from a startup at the brink of collapse to a billion-dollar B2B platform.

01

Read the terrain

Find the real constraints fast, where the money is leaking, where the team is stuck, and what the customer actually needs. No theater, no boil-the-ocean audits.

02

Stop the bleeding

Cut runaway spend, restore execution discipline, and get a win on the board quickly. I have taken 90% out of infrastructure cost in the first 30 days and meant it.

03

Build to outlast me

Recruit the talent, instill the culture, and ship the platform so the organization keeps compounding after the engagement ends. The goal is to make myself unnecessary.

Track record

Outcomes, not adjectives.

A few representative builds across healthcare, ad-tech, real estate, and enterprise SaaS.

Brandzooka
Chief Product Officer, Acting COO
2023 – 2025

Recruited as first CPO with the company at the brink of collapse. Stabilized operations, mentored a first-time CEO, then took over sales operations and turned the trajectory around, extending company viability by three years.

146% YoY revenue growth 78% burn reduction 90% infra cost cut in 30 days 93.7% net revenue retention
Strive Health
VP, Product Management · First Product Hire
2019 – 2022

Built a greenfield product organization to 20+ PMs and 90+ technical staff. Conceived and launched the CareMultiplier machine-learning platform driving cost savings and real clinical improvement, and guided product through a $140M Series B led by CapitalG.

+67% optimal dialysis starts −49% high-risk hospitalizations −36% 30-day readmissions −66% rural no-show visits
Homebot
First Product Lead
2018 – 2019

First dedicated product leader at the Denver fintech, later acquired by ASG. Distilled nascent goals into five integrated product lines, drove engineering velocity, and built the self-service growth engine.

245% MRR growth <5% churn +540% agent subscriptions +35% team velocity
Welltok
Chief of Staff · Director, Delivery Solutions
2013 – 2015

Second-in-command to the President and COO of a 120-person health-tech organization, later acquired by Virgin Pulse. Ran cross-functional deal management and scaled delivery from startup mode to enterprise-grade.

900% increase in deployments Record Q4 bookings IBM · Aetna · Kaiser scale
Meet High Camp

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Fractional CPOHead of AICOO · PE portfolio co.
The operator

I build product and technology organizations from scratch and drive them to outcomes that show up on the P&L and, in healthcare, in patients' lives.

I'm Rob McKinney, a Denver-based product and technology executive with roughly thirty years across greenfield startups and multibillion-dollar corporations. My pattern is consistent: enter the distressed or early-stage environment, stabilize it, and build the team and platform that keep compounding after I leave.

Hollis Mountain is where I do that work independently, as a fractional CPO/COO and a generative AI enablement practice serving founders and PE-backed portfolio companies. I'm a U.S. Navy veteran and former cryptologic technician, a 2025 HIRE Vets Gold Medallion recipient, and Head of Technology & AI Enablement on the board of VetXTherapy, a Colorado veteran-serving nonprofit.

Credentials
  • 30 yearsProduct, operations, and technology leadership
  • 3 acquisitionsBuilt during critical growth at Homebot (ASG), Examiner (AEG), Welltok (Virgin Pulse)
  • U.S. Navy VeteranCryptologic Technician · former TS/SCI clearance
  • 2025 HIRE Vets Gold MedallionThe only federal honor for veteran employment
  • PMP · CSPO · CSMCertified across product and agile delivery
  • B.S. Management Information SystemsUniversity of Arizona, magna cum laude · AI Laboratory research assistant
Let's talk

Got a hard climb ahead? Let's map the route.

Whether it's a turnaround, a greenfield build, an AI capability you need shipped, or a portfolio company that needs a seasoned operator, start with a conversation.

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