Bringing AI in at Headway

Choose between marked terms and open questions for buyer requests

Published Oct 29, 2026

You’re a forward deployed engineer working with Headway’s sales team. The team is in the room.

The setting

connects patients, outpatient mental health providers, and health insurers. gives health plans a network of credentialed clinicians who give outpatient mental health care, plus referral links and ways to measure how the network performs.

Discovery requests are entering expansion proposals alongside approved commercial terms.

Payer-specific proposals protect negotiation momentum, while standard terms protect the boundary around reporting commitments.

Who you’d be doing this for

“I took the reporting section to our committee, then found out two of those measures were still just requests.”

Kukua Akinwale · Behavioral Health Network Director · a character in this brief

Evaluates an expansion proposal for an existing payer partnership and needs to distinguish offered services from open negotiation points.

What is at stake

Five of eight payer deals contain requests beyond approved proposal language. You decide whether AI drafts those requests as marked terms or leaves them as questions for the seller.

Why it isn’t already fixed

Every obvious fix costs something else. That’s the part you’d have to decide.

  • account-specific language vs standard commercial terms
  • complete proposals vs unresolved buyer requests
  • research freshness vs contractual authority
  • reporting ambition vs delivery feasibility

Why Headway

Commercial line-of-business expansions join existing payer relationships to new expectations about outpatient network reporting.

Written with these in mind

Workflow-focused forward deployed engineersSolutions engineers working across commercial and product boundariesBuilders of source-grounded drafting systems

Not your kind of problem? 104 more at Headway, or browse every organization.

Where the organization context comes fromThe postings this brief was written from, and the reporting read before it.

The organization context comes from public information. The situation and characters are written for the brief.

Job postings it was written from

Public descriptions of the work at Headway. They are listed as sources, not as openings. The lines under a posting are its own words, where it meets this brief.

This is the setup. The work is inside.

Running it puts you in the room: the full situation and its constraints, stakeholders who push back in their own words, and the decisions that are yours to make. What you produce becomes a Day One Plan — work you can show someone instead of describing.

Other live briefs connected to this one, and what connects them.

Similar problems at other organizations

Like this one, each of these is about betting growth on an outside partner or launch.

The same setting, from another role

Each is set around Headway’s Headway for Payers, written for a different role. They’re separate briefs, not the same scenario.

Other problems with a similar purpose

In each of these, as in this one, the aim is to structure a partnership that creates real growth today and still holds up under pressure years later.