The work

Varied operating and applied AI engagements. Each one is shaped by what the situation actually needs, not by a fixed menu.

Both halves of the response

The AI-era operating response has two halves: the diagnostic that names which workflows redesign, retire, or hold; and the build of the tools that make the redesigned workflows actually run. Most firms do one or the other. Henry Street does both, inside the same engagement, on the same timeline, with the same operator carrying continuity across the two.

The shape of any given engagement is set by which halves the situation needs and how much of each. Some operators arrive needing the full diagnostic and a wholesale rebuild. Some have already named the bottleneck and want the build. Some need a single AI tool delivered into a workflow that the operator otherwise owns. The three registers below describe the work types Henry Street runs in; the engagement letter describes the specific scope.

Operating work

The diagnostic and redesign work Henry Street gets hired to do inside a mid-market company. Sometimes pure diagnostic: map the operations against what AI has changed about the cost stack, name the workflows that compress and the workflows that hold, deliver the bets the leadership team needs to choose between. Sometimes direct rebuild: the operator already knows where the pain is, and the work is rebuilding the thing. Sometimes phased across two or three quarters with milestones the engagement letter names. Sometimes embedded operator work during a leadership transition or a board-driven inflection.

The common thread: the work changes how the company actually runs, and Henry Street stays connected long enough to confirm the change held. Engagements that end at the deck stage and leave the rebuild to someone else are not what Henry Street is built for.

Common engagement shapes:

  • A six-to-eight-week diagnostic mapping the operations against the new AI cost stack and naming the redesign bets
  • A two-to-three-quarter redesign of a specific workflow (order-to-cash, fulfillment, vendor management, customer support) including any AI tools the rebuild requires
  • A three-to-six-month embedded operator engagement during a leadership transition, board inflection, or PE-led operating cycle
  • A pre-investment operating diagnostic for a PE operating partner placing a portco
  • A multi-phase operating engagement that includes a go-to-market system build in Phase 1 and a systems-integration phase running alongside or after

Applied AI builds

Discrete builds (agents, pipelines, internal tools, custom workflows) designed and shipped to solve a specific operating bottleneck the client has named. The working stack adapts to the build, not the other way around: Cloudflare Workers, Astro, KV, R2, VPS hosting for long-running daemons, vector databases for retrieval, the Claude API, OpenAI, and other LLM APIs are all in regular use across engagements. The right tools get picked for the job; the build is what the operator gets, not a stack tour. Builds ship into the client's real operating environment, not into a sandboxed demo. The build is the deliverable, not the deck.

Sometimes the build is standalone, because the operator owns the operating context already and what they need is the tool. Sometimes the build is bolted onto an operating engagement and is part of the redesign that engagement runs. Either way, the build is scoped at the start, shipped on a timeline, and handed off into the client's workflow with the documentation, training, and operating context the client needs to run it.

Builds shipped:

  • A prospect-and-client communication agent for fractional consulting and advisory practices, triaging inbound mail, drafting replies, and escalating when the situation requires
  • A legal-document anonymizer for PII handling in attorney workflows
  • A pay-application review system for multifamily construction back-office work
  • A legal knowledge base for litigation research and prior-case retrieval
  • An evidence curation workspace for family law and discovery-driven litigation

Builds in flight:

  • A construction-management agent for $20M+ developer-or-owner construction practices, currently in build

Partnership-shape engagements

Occasional, not default. Some opportunities are not actually engagements; they are partnerships. Different governance, different IP structure, different cadence, different counterparty paper. Henry Street takes this shape when the underlying opportunity warrants it and the structural fit is real, not as a way to make an engagement that doesn't pencil into something that does.

What partnership-shape looks like:

  • Co-developed product where Henry Street brings operating design and applied AI capability and the partner brings market access or a domain bench
  • Equity-and-cash hybrid where the cash covers the operator's time and the equity covers the asymmetric upside of a build that scales beyond a single engagement
  • Long-running operating involvement at partner-level governance rather than client-vendor structure

What Henry Street does not do

Fit recognition matters. Engagements that fit produce work that holds; engagements that don't, don't. The firm is direct about the ones it does not take.

  • Open-ended fractional COO retainers. Henry Street engagements are scoped, with the scope named in the agreement and a defined end-state.
  • Generic strategy decks. The deck, if one exists, is a byproduct of the operating work, not the deliverable.
  • AI training or workshops as a primary offering. Henry Street is built around designing and shipping operating change, not training other operators to design it themselves. Training on systems Henry Street ships is part of the engagement; training as a standalone service is not.
  • Equity-only engagements as a default. Case-by-case exceptions exist when the structural fit is real, but the default shape includes cash.
  • Implementation-only work handed in from another firm's strategy. Henry Street designs the operating change and builds the implementation; running someone else's deck through the build phase is not what the firm does.

How engagements run

  1. 01

    Scoping conversation.

    Engagements start with a 30-minute conversation. It is free, it is direct, and it is for both sides to figure out fit. Henry Street hears the operating situation; the operator hears how the firm thinks about it; one of you decides whether to keep going.

  2. 02

    Proposal and agreement.

    When the fit is real, Henry Street writes a proposal that names the work, the deliverables, the timeline, and the investment. Pricing is set per engagement based on what the work actually requires; the firm does not publish indicative fee ranges because the scoping conversation does that work first. The engagement is papered as a single agreement or as an MSA + Order Form + SOW, depending on the engagement shape.

  3. 03

    Doing the work.

    Engagements run on a cadence the agreement names. When an engagement needs additional hands beyond Ben, Henry Street partners with named specialists and the agreement says so. The firm does not pretend to have a team it does not have, and it does not hand off the messy parts to someone else's implementation shop.

Get in touch.

If the work above fits the situation you are in, the next step is a 30-minute scoping conversation. It is free, and the firm only takes the engagement if the work fits.

Start the conversation →