Miles Gullingsrud Strategic initiatives · AI-native operator

I build structure where there isn't any — then run it.

Miles Gullingsrud. Operator for ambiguous, high-stakes problems.

Strategic initiatives leader for the work that has no playbook.

Twenty years turning high-visibility, ambiguous problems into executed outcomes. I frame the question, align the executives, drive the cross-functional work, and own the result — from AI transformation to payments operations at scale.

See the proof Get in touch

Based in

San Francisco Bay Area

Currently

VP, Finance Operations · Invisible

Prepared for

Visa · North America Executive Office

The difference

I don't advise from the sidelines. I build the thing, then operate it.

Throughout my career I've been drawn to a particular kind of work: big problems that lack clear structure, an obvious owner, or an established approach. I step into that ambiguity, build the framework, drive the alignment, and see the work through until the outcome is real.

I'll be direct about one thing. I don't have a management-consulting pedigree. What I have instead is the muscle of an operator: I've built the systems, then owned and run them at scale. You won't get that from someone who hands over a deck and leaves.

That combination — strategist who can frame the problem, operator who can make the answer stick — is exactly what I bring.

Miles Gullingsrud

Selected work

Four problems with no playbook — framed, built, and owned to outcome.

Each one maps directly to what the Strategic Initiatives Lead role calls for: AI transformation, building from zero, executive credibility, and running it at scale.

The first project-level P&L in the company's history

VP, Finance Operations · Invisible

Invisible was delivering millions of dollars of project work per month across 100+ client projects — with no way to measure profitability at the project level. I defined the business problem, found the gaps in how data was captured, restructured the data schema and the business processes behind it, and designed the first project-based P&L reporting system.

100+

client projects brought into one profitability view

1st

project-level P&L visibility ever, for execs & account teams

Maps toBuilding from zero — structure where there wasn't any.

AI transformation, architected — not just championed

VP, Finance Operations · Invisible

I'm standing up the AI program for the Finance function right now: designing production workflows, building an automation roadmap across NetSuite, Salesforce, and in-house tools, and authoring the FinOps 2026 mission, vision, and four-pillar strategy. I drove alignment across CEO, CFO, CTO, and Head of Product — and represented the company at EY's AI for Finance Summit.

core systems targeted for AI-leveraged automation

C-suite

alignment driven across CEO, CFO, CTO & Product

Maps toEmbedding AI across the business — operating model, metrics, change management.

Payments operations at scale, de-risked

VP, Finance Operations · Invisible

I own bi-monthly payment operations for 5,000+ AI training experts and $1.5M+ in bi-weekly disbursements. I identified and resolved chronic, high-risk process vulnerabilities affecting 10,000+ experts, then drove Expert Pay Automation onto the Q2 product roadmap.

$1.5M+

in bi-weekly disbursements under ownership

10,000+

experts protected from a high-risk failure mode

Maps toOwning the messy, high-stakes operational problem end-to-end.

Board-level credibility, on both sides of the table

VP of Operations · WRA, Inc.

I served simultaneously as an Employee Director on the Board and as the VP presenting strategy and operations to that same board. I led 12 Principal Team Leaders over 80+ professionals and a 500-project annual portfolio, deployed an ERP supporting $20M in revenue, and moved employee engagement from the 35th to the 65th percentile on Gallup Q12.

35→65

percentile jump in employee engagement (Gallup Q12)

$20M

revenue supported by the ERP I deployed

Maps toExecutive presence — clear, credible, calm when stakes are high.

What I bring

The operator's toolkit.

A repeatable way of working that holds up across Finance, Operations, Technology, and People functions.

Building from zero

Operating models, programs, and infrastructure that didn't exist before — built to hold up at scale.

AI transformation

I architect the workflows and run the change management to make adoption stick — not advocate from the sidelines.

Structuring ambiguity

Turning messy, undefined inputs into a sharp problem statement and a clear point of view leadership can act on.

Cross-functional execution

Coordinating Finance, Engineering, Product, and People Ops to drive an outcome across the whole org.

Executive & board engagement

Board-director and VP-presenter experience — clear and credible whether presenting, pushing back, or thinking on my feet.

Operating at scale

Payments, P&L, ERP, and budgets in the eight-figure range — run with control, accuracy, and accountability.

20+

years turning ambiguity into executed outcomes

5,000+

experts paid across bi-monthly operations

$20M

revenue supported by an ERP I deployed end-to-end

80+

professionals led across a 500-project portfolio

Track record

Twenty years of building and running, across very different rooms.

2024 — Now

Vice President, Finance Operations

Invisible · AI enablement services

Pioneering AI adoption across Finance, building the project-level P&L and executive dashboards, and owning payment operations for thousands of experts. Scaling the function from inception into autonomous process owners.

FinOps 2026 strategy author EY AI for Finance Summit $1.5M+ bi-weekly disbursements

2019 — 2024

Vice President of Operations

WRA, Inc. · environmental consulting

Concurrent Employee Director on the Board and VP-level executive presenter. Led 12 Principal Team Leaders over 80+ professionals and a 500-project portfolio; deployed a $20M-revenue ERP and lifted engagement from the 35th to 65th percentile.

Board of Directors $20M ERP deployment 35→65 percentile engagement

2018 — 2019

Director of Operations

The Trium Group · leadership development consulting

Built the operational infrastructure behind the firm's consulting delivery: redesigned talent acquisition to cut time-to-decision by 50%, and implemented a cloud-first technology strategy for a distributed workforce.

2015 — 2018

Head of Internal Operations

AltSchool, PBC · ed-tech startup

Built operational infrastructure for a startup scaling from concept to 7 micro-schools nationally in 3 years. Managed a $2.2M budget with 20% cost reduction two years running and a 50% promotion rate among direct reports.

2009 — 2015

Finance & Administration Director

Adams & Associates · Dept. of Labor operations contract

Ran an $18M annual operating budget to a 0.25% variance. Built a procurement and audit control system that cut delivery time 43% and raised audit scores 15%, leading 8 managers and 45+ staff.

2003 — 2007

Professional Applications Consultant

Dekker, Ltd. · project management software

Managed the firm's largest annual client contract ($2.5M, United Space Alliance), driving growth through consultative sales, needs assessments, and solution implementation.

Certification

Professional Coaching

New Ventures West · 2020–2021

Certification

Project Management

University of Phoenix · 2003–2004

Degree

B.A., English

UC Riverside · 1997–2001

Let's talk

The work you're describing is exactly the work I do.

You described someone who can parachute into priority problems, build structure where there isn't any, and drive outcomes across functions without being handed a script. I'm built for that. I'd welcome the chance to talk about whether it's the right fit for what you're building.

Email me Call · 415-269-5929 Download résumé

miles.gullingsrud@gmail.com

Phone

415-269-5929

Location

San Francisco Bay Area, CA

/in/milesdonaldgullingsrud