Dale Bailey
Dale D. Bailey
VP, Post-Sale Revenue & Services

I scale post-sale organizations.
And I've written down
what I've learned.

Twenty years building and leading customer revenue functions in healthcare SaaS. Author of the Trust → Growth™ framework. Currently in selective search for VP Customer Revenue / CCO roles.

Read the framework

Operator first.
Author second.

I've spent 20+ years leading post-sale organizations in healthcare SaaS — building and scaling Customer Success, Professional Services, and Support under unified P&L ownership at companies from $4M to $500M+ ARR.


At Halo Health, I built the post-sale revenue engine from zero, delivering 120%+ NRR and negative churn as we scaled from $4M to $12M through acquisition. At symplr, I unified four acquired delivery organizations into one operating model, owning a $30M+ P&L and a $150M+ customer portfolio through 18 months of post-M&A integration while sustaining NRR and driving 50% delivery cost reduction.


After symplr, I took an intentional pause. Time with family, a mental reset after years of operational intensity, and space to document two decades of post-sale experience into the Trust → Growth™ framework. It's a model for how customer trust becomes the leading indicator of revenue: protect what you have, grow from within. Now preparing for the next chapter.

Trust → Growth™

The accounts that renew and expand aren't the ones with the highest usage. They're the ones with the highest trust. The Trust → Growth™ framework is a customer revenue maturity model built on that thesis — trust as the leading indicator, value realization as the proof, earned growth as the consequence.


The framework organizes customer revenue across three continuous conditions: Trust (protect), Realization (value delivered), and Growth (earned expansion). Not lifecycle stages. Not a playbook. A diagnostic and execution system.


Most customer success platforms track what already happened. The Trust → Growth model tells you what's about to happen — and what to do about it.


Read the framework →

Assessment
Customer Revenue Maturity Diagnostic
A rigorous maturity diagnosis of a company's customer revenue operating model, delivered as an advisory engagement. Scores the organization across Trust, Realization, and Growth dimensions, surfaces the specific gaps blocking progression, and produces a prioritized 90-day roadmap for the changes that actually move the number.
Manage
Trust-Led Growth Platform
The operational platform that runs on top of the framework — a live picture of every customer relationship, with trust scoring, stakeholder maps, risk signals, and intervention tracking. Turns customer trust from a soft metric into the leading indicator the org actually operates against.

Cultivate — an AI Transformation OS.

A working prototype I built to test a hypothesis: AI transformation is a portfolio management problem wrapped around a change management problem — and the missing piece for the Chief AI Officer isn't another dashboard. It's a coach.


Cultivate gives the person holding the AI mandate a shaped pipeline (Seed → Sprout → Bloom → Harvest → Compost), a six-layer governance model with decision governance at the center — recommend vs. decide vs. execute — and an AI coach named Della who runs the weekly cadence. She pulses owners, surfaces at-risk bets, and demands an honest kill or a realized number on every initiative.


Same operator instinct as Trust → Growth™: a few fundamentals, well-run, beat any amount of tooling without them. The domain is different — Cultivate is designed for the AI transformation office inside a regulated enterprise, where safe scale is the constraint and the bar for clinical, financial, or customer-facing AI is higher than a Copilot pilot.

Failure Mode A
All ideas, no structure
Slack is full of "wouldn't it be cool if." Hackathons generate demos that never ship. Energy, no cadence, no owner, no kill criteria, no line from idea to outcome.
Failure Mode B
All structure, no ideas
A governance committee. A policy document. A risk framework. Maybe a CAIO. But the pipeline is empty. Every idea dies in a review gate. Adoption is zero and the committee is measuring its own meetings.
The Fix
A coach that runs the cadence
Della drives the Monday pulse and the Friday harvest. She remembers what you committed to last week and asks about it this week. The governance enables safe scale; the cadence enables honest outcomes.
Cultivate cockpit showing AI portfolio for Mercy Health Network
Cockpit
Live operating cockpit

Where the AI transformation office runs from. Della's maturity diagnosis on two axes (Ideas × Governance), portfolio health, and the next move — not a generic "what should I do" prompt, but a specific recommendation grounded in the org's current state. Demo data shows a healthcare network with $3.3M in flight and $2.8M realized across the portfolio.

  • 3×3 maturity matrix with named positions (Dormant → Operating Model)
  • Della scores you and recommends the next move
  • Portfolio totals: in-flight, realized, stage distribution
The Plot - Cultivate kanban showing AI initiatives across stages
The Plot
Approved bets in motion

Staged kanban across Sprout → Bloom → Harvest → Compost. Each card carries owner, value theory, risk tier, and success metric. Every initiative ends in a realized number or an honest compost — no zombies in the garden. The Compost column is a feature, not a failure.

  • Owner, value, risk, and metric on every card
  • Filters: at-risk, unowned, needs metric, high-value
  • Honest kill criteria, not silent decay
Cultivate governance queue with pending approvals and security review gates
Governance
Governance that enables safe scale

Six-layer model — use case, data, model, workflow, decision, and measurement. Pending bets route through committee sign-off with security/privacy and data-owner gates before they can advance. The piece most companies miss is decision governance: defining for every initiative whether AI can recommend, decide, or execute. Designed to unblock, not block.

  • Six-layer fence with decision governance named explicitly
  • Approval queue with security/privacy and data-owner gates
  • Audit trail: model version + prompt + reviewer + override

Applied AI experiments.

Alongside Trust → Growth™ and Cultivate, I've been applying AI to adjacent problems — primarily in career management and post-sale operations. Working prototypes, not products I'm selling. They're how I've gotten fluent with modern AI development — agent orchestration, structured scoring, cross-app context — and they inform how I think about building AI-native tools for revenue and operating teams.


Representative work includes a career operating system (job scoring, networking intelligence, interview prep, portfolio-level pipeline visualization) with a cross-app AI layer for pattern detection and proactive recommendations — the same coach-not-dashboard pattern that shapes Cultivate. Screenshots in the next section.

Applied work.

Screenshots from the framework software and adjacent AI experiments. The Trust → Growth platform is the primary focus. The career-management work is how I've gotten fluent with AI development.

Trust → Growth™ — The Framework Platform
An assessment + operational platform for customer revenue leaders. Diagnose the company, then operate the book of business through the Trust/Realization/Growth model.
Primary focus
Trust to Growth assessment dashboard
Assessment
T→G Assessment

A rigorous maturity diagnosis of a company's customer revenue operating model. Scores the organization across Trust, Realization, and Growth dimensions, surfaces operating-model gaps, and produces a prioritized 90-day roadmap. Delivered as an advisory engagement.

  • Trust, Realization, and Growth index scoring
  • Operating-model gap analysis
  • 90-day roadmap and exec readout
Trust to Growth customer portfolio
Manage
T→G Manage

Continuous portfolio intelligence for a customer revenue org. Trust, realization, and growth signals scored across the full book of business; the system surfaces which accounts need action and suggests the intervention. AI is running the monitoring loop, not assisting the CSM after the fact.

  • Portfolio-level Trust Index
  • Signal log and intervention engine
  • Stakeholder mapping and renewal tracking
Applied AI experiments
Working prototypes — not products for sale. How I've gotten hands-on with AI development while codifying the framework.
Reference work
Career portal with AI insights
Prototype
Career Operating System

Cross-app AI layer for career management. Runs pattern detection across job pipeline, networking activity, and reflection data — producing proactive recommendations rather than reactive chat.

Shortlist AI job scoring
Prototype
Structured Scoring

AI applied to weighted scoring across multiple criteria. Demonstrates how to build opinionated evaluation frameworks rather than generic LLM wrappers.

Networking intelligence
Prototype
Relationship Intelligence

AI-powered contact sourcing and outreach generation. Informs how signal and context can be woven into relationship-management tooling for customer revenue teams.

Operator principles.

The Trust → Growth™ framework sits on top of a set of operating beliefs earned across 20 years of post-sale work. These are the principles that make the framework credible — and the lens I bring into every engagement, hire, or org build.

Trust is the leading indicator

Most customer revenue orgs measure lagging signals — health scores, NPS, last-90-day usage. By the time these move, the relationship has already decided. Trust is what actually predicts what comes next, and the only metric worth building an operating system around.

Diagnose before you intervene

Most operating problems aren't a tooling problem. They're a sequencing problem. Before you redesign a function, instrument a playbook, or roll out an AI agent, you need an honest picture of where the operating model breaks down. Diagnosis first, intervention second.

Systems, not heroics

Heroic CSMs save individual accounts. Systems save books of business. Everything I've built — at Halo Health, at symplr, and in the Trust → Growth framework — has been about turning repeatable operator judgment into infrastructure that scales past any single person.

Let's talk.

In selective search for VP Customer Revenue, VP Post-Sale, Chief Customer Officer, or AI-transformation leadership roles where operator experience, the Trust → Growth™ framework, and AI-native tooling can compound into real retention, expansion, or safe-scale outcomes. Healthcare and regulated-enterprise contexts are a natural fit. Based in Cincinnati; open to remote, hybrid, or relocation for the right role.

Also open to a conversation if you're scaling a post-sale organization, navigating post-acquisition integration, or thinking through how AI agents change the customer revenue or transformation operating model.