For operations leaders

Make AI pay off in your operation.

You were told to use AI. Now you need results. I find the workflows where it pays for itself, get the first one live with your team, and hand you numbers finance will accept.

Book a 30-minute callTake the 2-minute scorecard

No pitch. If I can’t find a workflow worth automating, I’ll tell you on the call.

Now
Head of Strategic Operations at Checkr
Before
Seven years running Lyft’s global support platforms
Also
Building Chief and publishing Models at Work
The run sheetEvery engagement
  1. 01
    Map the work
    Volume, cost, error rate, who touches it
  2. 02
    Pick the targets
    Eliminate, automate, or leave to people
  3. 03
    Prove it small
    One workflow, real cases, a baseline
  4. 04
    Roll it out
    Training, escalation paths, trust
  5. 05
    Measure and tune
    Numbers leadership can act on
Start with the pain, not the model. Keep people on the edge cases. Measure everything.
Why operations leaders work with me
Owned the budget
Ran the tooling P&L for a 20-person operations org at Lyft. I know the questions finance asks before they fund anything.
Bought and rolled out the platforms
Led the Zendesk, 8x8, and Twilio Flex migrations across 12 sites, from vendor evaluation to the day the floor switched over.
Put AI into live workflows
Two years taking AI from pilot to daily use in support and operations, and I build with it every week.
Still in the seat
Head of Strategic Operations at Checkr today. The advice comes from current practice, not a slide library.

Experience with teams at

checkr
College Bound
HuckleHuckle
Lyft
Links
OpenWeb
QualiFi'd
Who this is for

Built for the person who owns the operation, not the person selling the software.

You have volume you can measure, a team that does the work, and nobody whose actual job is making AI deliver. If that is you, one of these will sound familiar.

Founder doing the COO job yourself? Here is how that works.

Probably not a fit if
  • You want someone to build an AI product for customers (I do operations, not product engineering)
  • You want a vendor's implementation partner who will only recommend their tool
  • You do not yet have a workflow that runs a few hundred times a month
Sound familiar?

Most AI efforts stall somewhere between the demo and the daily workflow.

That gap is an operations problem, not a technology problem. It closes when someone maps the actual work, sets a baseline, gets one workflow live with the team, and measures it honestly.

01

Licenses bought, usage faded

You rolled out the AI seats. Usage peaked in week two. Now the CEO wants to know what the company got for the spend, and the honest answer is a few power users and a lot of logins.

02

Three pilots, none in production

Each one has a champion, a vendor, and a slide. None has a baseline, so nobody can say whether it worked, and nobody wants to be the one to kill it.

03

ROI you cannot defend

The vendor's "hours saved" number will not survive a finance review. Your team's real gains are anecdotes. Budget season is coming either way.

I have been on your side of every one of these: the person the vendor pitched, the person who had to make the rollout stick, and the person who had to explain the numbers afterward.

How I can help

Three ways to work together, scoped to where you are.

Every engagement starts with the work your team already does and ends with numbers. No slide-only strategy.

AI Operations Assessment

2 to 3 weeks

Find the handful of workflows where AI will pay for itself this quarter.

I sit with your team, map how the work actually flows, and score every candidate on volume, cost, error rate, and risk. You get a short list, not a long one.

  • Workflow map with volume, cost, and failure points
  • Scored opportunities: eliminate, automate, or keep human
  • Build, buy, or wait call for each one
  • A sequenced plan with owners, metrics, and a budget range
Best forLeaders who have been asked to "do something with AI" and want a defensible answer.Details and FAQ →
Most requested

Pilot to Production

6 to 12 weeks

Take one workflow from idea to something your team uses every day.

One workflow, end to end. I design it, pick or build the tooling, set up the review loops and guardrails, train the team, and measure it against the old way.

  • Working automation in your stack, with human review where it matters
  • Vendor selection or a build, with the tradeoffs written down
  • QA, escalation paths, and a rollout plan the team helped shape
  • Before-and-after numbers leadership can trust
Best forTeams with a clear target and a stalled or unstarted pilot.Details and FAQ →

Fractional AI Operations Lead

Ongoing, part-time

An owner for AI in operations without a full-time hire.

I run the AI roadmap for your operation: what gets automated next, which vendors stay, how adoption is tracked, and what gets reported up. A few days a month, consistently.

  • A living roadmap tied to operating metrics
  • Vendor and tool management, including renewals and exits
  • Monthly measurement and a clear readout for leadership
  • Team enablement: playbooks, training, office hours
Best forOperations orgs with momentum that need someone to keep it honest and moving.Details and FAQ →
Not sure which fits? Let’s talk

Most people start with the assessment. If the target is already obvious, we skip straight to the pilot.

How it works

An operator's playbook, not a strategy deck.

The same sequence every time, because it works. It is built from running support platforms at Lyft scale and from the last two years putting AI into real workflows.

Working principles
  • Start with the pain, not the model.
  • People own the edge cases.
  • If it isn't measured, it didn't happen.
  • Compliance is infrastructure, not an audit.
  1. 01

    Map the work

    Before anyone picks a tool, we know the volume, cost, cycle time, and error rate of each workflow, and who touches it. Most of this comes from your ticketing data and an afternoon with the team.

  2. 02

    Pick the right targets

    Every candidate gets sorted: eliminate the work that should not exist, automate what is routine and well defined, and keep people on the cases where judgment or risk is high. The best AI project is often the one you do not need.

  3. 03

    Prove it small

    One workflow, real cases, a baseline to compare against, and a human reviewing output until the numbers earn trust. Build or buy gets decided here, with the tradeoffs written down.

  4. 04

    Roll it out like you mean it

    Training, documentation, escalation paths, and a feedback channel the team actually uses. I started my career as a teacher. Adoption is a teaching problem before it is a technology problem.

  5. 05

    Measure and keep tuning

    A dashboard leadership can read in a minute: what was automated, what it cost, what it saved, and where it was wrong. Then we tune, expand, or kill it. Nothing runs unmeasured.

Where this comes from

Twelve years on the operations side of the table.

I have bought the platforms, run the migrations, owned the tooling budget, and been accountable for the numbers afterward. That is the seat I bring to your AI work.

checkr2026 to present
Head of Strategic Operations

Leading strategic operations at Checkr, the AI-powered background check platform, where automation, accuracy, and compliance have to coexist on every case.

  • Operational strategy for regulated, high-volume workflows
  • Automation and human review designed together, with FCRA in the room
  • Cross-functional ownership across product, support, and engineering
OpenWeb2025 to present
Senior Product Consultant

Product operations for a B2B platform serving major publishers. Built the operating model and measurement system that let product, engineering, and publisher success ship a new Forums product to partners.

  • Launch playbooks and partner onboarding workflows
  • Event schema, KPIs, and dashboards teams actually use
  • Decision frameworks and execution rhythm across five functions
Links Golf Club2023 to 2025
Head of Product

Led product and operations for a global membership platform with 60,000+ members. Selected and implemented the identity, payments, pricing, and event platforms, and brought AI into support and operations workflows.

  • AI-enabled workflows that cut manual load and sped up execution
  • Vendor evaluation, contracting, implementation, and P&L accountability
  • Feedback routing from support and partners into product decisions
Lyft2016 to 2023
Senior Manager, Support Product Programs and CX Platforms

Owned product operations and the tooling P&L for Lyft's global customer experience platform: 500,000+ monthly contacts, 12 sites, and a 20-person org across product, engineering, systems, and operations.

  • Led the Zendesk, 8x8 IVR, and Twilio Flex migrations end to end
  • Self-service and automation programs that reduced avoidable contacts
  • Voice of customer synthesis that drove roadmap prioritization
Huckle2014 to 2016
Co-Founder and Head of Product

Co-founded a venture-backed consumer software company and took it from zero to 50,000 users across iOS, Mac, web, and API, with release discipline that kept unplanned downtime at zero.

  • Product vision, roadmap, and team process from scratch
  • Launched on stage at Launch Conference after the inaugural Launch Incubator
College Bound2013 to 2014
Director of Innovation

Led the zero-to-one build of Bridgit2College, a college access platform funded by the Dell Foundation, turning one-to-one counselor interventions into automated, scalable workflows.

  • Rolled out to 4,000 students and 40 counselors
  • Randomized control trial showed a measurable lift in college enrollment
What I'm building

I don't just advise on AI adoption. I run two things that depend on it.

Both are live, both are mine, and both shape the advice you get: one tracks how companies really use AI, the other ships AI workers that have to earn their keep.

Greg Hill

Greg Hill

Session Player Studio, Nashville

gregory@sessionplayer.studio
About

I started as a teacher. Everything since has been some version of the same job: getting a group of people to change how they work, and making sure it sticks.

I have spent twelve years in operations and product roles where the technology was never the hard part. At Lyft I ran the platforms behind half a million support contacts a month and led three major system migrations. At Links I owned vendor selection and the P&L for every platform we ran, and was the first to put AI into the support workflow. At OpenWeb I built the operating model that got a new product to enterprise publishers. Today I lead strategic operations at Checkr.

Along the way I started building with AI myself: classifiers for customer pain, internal tools, and agent workflows that I use every week. So I can sit in the vendor meeting, read the output, and tell you honestly whether it is ready for your team.

The name comes from Nashville session players: the people who walk in, learn the song fast, play exactly what it needs, and make the record better without needing to be the star.

Session notes

How I think about the work.

Short, practical notes from real operating problems.

All notes →

Explore Session Player Studio

Questions

The things people ask on the first call.

Yes, and that is a common starting point. We map where the licenses could actually change a workflow, set a baseline, and roll out a specific use case with training and a review loop. Seats that are sitting idle become a measured workflow or get cut.

No. Most of the wins in operations come from well-defined workflows and off-the-shelf tooling configured carefully. When something does need to be built, I can build the first version myself or write the spec your engineers will actually thank you for.

I am vendor-neutral. I have bought and implemented platforms like Zendesk, Twilio Flex, and 8x8 at Lyft scale, and I build with Claude, OpenAI, and the current generation of agent tooling every week. The recommendation follows the workflow, not the other way around.

Assessments are fixed fee. Pilots are scoped and priced as a project. Fractional work is a monthly retainer for a set number of days. I will give you a number on the first call once I understand the scope.

It is the norm for me. I currently run operations under FCRA, and at Lyft I worked through regulatory programs that required careful tradeoffs. Compliance gets designed into the workflow, with audit trails and human review, rather than bolted on after.

Agencies sell builds. I sit on your side of the table: I have been the operations leader who had to make a vendor's promise real for a team of two hundred. The goal is adoption and measurable results, not a demo.

A short list of scored opportunities, one workflow live with human review, and a before-and-after readout on volume, cycle time, error rate, and cost. Teams usually see their first number inside the first month of a pilot.

Usually within two to three weeks of a first call. An assessment takes two to three weeks from kickoff, and most pilots show their first numbers inside the first month.

Contact

Let's find the first workflow.

Thirty minutes is enough to tell whether there is a real opportunity and which engagement fits. No pitch.

or send a message

What You Get

  • →An operator who has bought, built, and rolled out the tools, not just advised on them
  • →A short list of workflows worth automating, with the numbers to back it
  • →Direct access. No account managers, no junior team
  • →Fixed-fee assessments, scoped pilots, or a monthly retainer

Direct Line

Email
gregory@sessionplayer.studio
Based In
Nashville, works anywhere