OxerLineAdvisory

Running a tech team you didn’t build?

I’m an operator who speaks tech. Whether you’re covering the CTO seat or just stepped into it, I keep the commitments on track through the handoff.

Contact me
The Work
Where I Come In

When the CTO seat is open and engineering reports to you now.

When you’re the new CTO, holding commitments you didn’t make.

When the business keeps making promises and nobody can say which ones will land.

Your C-Suite makes a commitment. Your engineers build a reality. What happens when they diverge? With technology moving this fast, you can’t put the business’s promises on hold for months.

My Promise

  • One problem. One deliverable. Nothing open-ended.

  • I test every fix with the people who have to live with it. My job isn’t done until it sticks.

  • I’m not here to take the CTO seat or run the team. When I’m done, I leave, and the team keeps everything I built.

Two Moments, One Practice
The Mandate

I review what each team is building and what the business has promised. You get plain answers on what will land, what threatens it and what has to be decided now. Then I do the groundwork the next leader will need, hands-on.

The Exit

You can see what each trade-off will delay. The next leader inherits a written record of what’s been promised and who owns each open decision.

Deliverables
  1. One list of every initiative, with named owners
  2. A leadership view of what’s being built and why
  3. Open decisions, each with an owner and a date
Real Life Outcome

Six consecutive quarters without a reprioritization fire drill across 50+ engineering pods.

The Mandate

I work to your priorities. In a few weeks you get a picture of what you’ve inherited and what’s already been promised, from engineering, product, sales and finance. Then I help carry out the fixes you choose.

The Exit

You own a plan the business believes, sooner. The team keeps everything I built.

Deliverables
  1. Inventory of inherited commitments
  2. A short list of fixes, ranked by you
  3. Hands-on help carrying them out
Real Life Outcome

When a new CFO and CTO arrived at a healthcare data platform: rebuilt the software capitalization policy and won auditor sign-off on $15 million in additional capitalized software.

Scope an engagement
Track Record
HR SOFTWARE COMPANY, SERIES E

75 new clients starting 1/1 had been sold the new payroll product; ~1,100 existing clients and Customer Service leadership weren't ready. Sales wanted rollout; Service wanted to stop it. Brokered a phased rollout across Sales, Service and Technology (new implementations as a live test) that met new-client commitments without a code freeze.

HEALTHCARE DATA EXCHANGE PLATFORM, PRE-EXIT

Overhauled software capitalization policy, secured external auditor sign-off and eliminated ticket-level time tracking. Unlocked $15 million in incremental capitalized software.

NYSE-LISTED HEALTH INSURER, ENTERPRISE SCALE

Built portfolio visibility and budget tracking across 50+ engineering pods. Six consecutive quarters without reprioritization fire drills.

NYSE-LISTED REIT, SMALL-CAP

Redesigned internal financial controls system, achieving a 35% reduction in tested controls while maintaining Sarbanes-Oxley compliance.

Be the next success story
About Clare
Credentials Harvard Business School, MBA CPA, Massachusetts · License #26079
Companies Oscar Health · Datavant · Namely · EY · Citigroup
Operating Scale $200M+ Engineering & Product Budgets
Clare Hawthorne, Principal of OxerLine Advisory

Clare Hawthorne

I’m an operator who speaks tech. I’ve spent 20 years building within and across technology, finance, HR and operations teams.

I can tell when finance and engineering, or product and sales, walk out of the same meeting with different ideas of what they just agreed to. I’ve spent my career in that room, translating until both sides will sign the same plan.

I have no stake in which side wins the argument, so I can tell you what I actually see. I get my hands dirty, then leave behind something the team can build on.

I co-wrote Deliberate Compliance (IT Revolution, 2026) and write Call It Early, a newsletter about what goes wrong inside organizations.

Work with Clare

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