Areas of work

Four places revenueis won or lost.

These are areas of work, not packages. I start by diagnosing the actual commercial problem, then put my time where it creates the most value.

01 · Land

New logo acquisition.

Explore new customer acquisition →

The business problem

Pipeline is thin or hard to predict. New business still comes from the founder’s network rather than a motion the team can repeat. People are busy, but it isn’t clear who to pursue, what to say, or why deals stall.

What I actually do

  • Define the ideal customer profile
  • Sharpen positioning and messaging
  • Shape the go-to-market strategy
  • Build prospecting and pipeline generation
  • Tighten the sales process and conversion
  • Work deals alongside the team
  • Raise sales team effectiveness

What you get

  • A documented ideal customer profile
  • Positioning and messaging the team actually uses
  • A defined sales process with clear stages
  • A pipeline you can inspect, not guess at
02 · Retain

Customer retention.

Explore customer retention →

The business problem

Customers renew late, quietly downgrade, or leave without much warning. Sales, onboarding, and customer success each own a piece of the relationship, and nobody owns the whole of it.

What I actually do

  • Review renewal performance
  • Analyze churn and what drives it
  • Align customer success with sales
  • Fix commercial handoffs
  • Define account health
  • Improve the customer experience where it touches revenue
  • Build retention processes

What you get

  • A clear view of why customers stay and why they leave
  • Account health measures the team reviews
  • Defined handoffs between sales, onboarding, and success
  • A renewal process that starts early, not at the deadline
03 · Expand

Account expansion.

Explore account expansion →

The business problem

Existing customers would buy more, but nobody is responsible for finding it. Expansion happens by accident, packaging makes it awkward, and account plans exist only for the largest names, if at all.

What I actually do

  • Set account growth strategy
  • Identify expansion opportunities
  • Design upsell and cross-sell motions
  • Review pricing and packaging
  • Lead account planning
  • Tie expansion to the value customers realize
  • Build the expansion sales motion

What you get

  • A prioritized view of expansion opportunity across the base
  • Account plans for the accounts that matter
  • Pricing and packaging that make buying more straightforward
  • An expansion motion with a clear owner
04 · Lead

Fractional CRO leadership.

Between CROs? See CRO Transition Support →

Explore fractional CRO leadership →

The business problem

The company needs senior commercial leadership but isn’t ready for, or can’t yet justify, a full-time CRO. Or the CRO has left, and revenue can’t wait for the search to finish.

What I actually do

  • Set commercial strategy and priorities
  • Own revenue accountability
  • Lead sales and develop the team
  • Run pipeline management and forecasting
  • Establish the operating cadence
  • Coordinate sales, marketing, product, and customer success
  • Execute alongside the team

What you get

  • An experienced commercial executive in the room
  • One person accountable for the revenue plan
  • A forecast built on inspected pipeline
  • A weekly and monthly operating rhythm

Not sure which of these is the real problem? That’s what the Commercial Diagnostic is for →

Other challenges, such as making revenue repeatable, proving scalability to investors, and aligning commercial teams, are covered in Growth Challenges.

How to engage

Three ways to work together.

Any of them can cover one area of work or several.

Fixed scope

Commercial Diagnostic

A focused, fixed-scope assessment of commercial performance.

What I do

  • Review the relevant commercial data
  • Interview stakeholders
  • Assess commercial constraints
  • Identify opportunities
  • Prioritize recommended actions

What you receive

  • A clear assessment of what’s working, what isn’t, and what should change
  • An actionable set of priorities
  • A defined project, not an ongoing retainer

Indicative investment

$3,500–$5,000
Fixed fee

Credited toward the first month of a Commercial Build if you continue.

Hands-on execution

Commercial Build

Hands-on work to build, repair, improve, or scale a specific commercial capability.

What I do

  • Work alongside the team
  • Design and implement improvements
  • Test assumptions
  • Measure performance
  • Refine the commercial motion
  • Help establish repeatable practices

What you receive

  • Measurable progress
  • Capabilities and processes the organization keeps using

Indicative investment

$5,000–$10,000
Per month
Embedded leadership

Fractional CRO

Embedded executive commercial leadership, without a full-time CRO.

What I do

  • Lead commercial priorities
  • Work directly with founders, CEOs, and leadership teams
  • Coordinate commercial execution across functions

What you receive

  • Experienced executive leadership
  • A structured operating rhythm

Indicative investment

$10,000–$25,000
Per month

Indicative ranges, not fixed prices. The actual scope and fee are set after an initial conversation about what the business needs.

After we start

What the first 90days can look like.

An illustration, not a fixed program and not a guaranteed outcome. Commercial Build and Fractional CRO engagements may continue well beyond 90 days.

Days 1–30
Understand and prioritize.
  • Review performance
  • Meet stakeholders
  • Identify constraints
  • Agree on priorities and success measures
Days 31–60
Execute and improve.
  • Work alongside the team
  • Address priority problems
  • Test assumptions
  • Measure early progress
Days 61–90
Refine and institutionalize.
  • Establish repeatable practices
  • Create operating rhythms
  • Agree on next priorities

D²BT remains the operating method underneath every engagement. See the method →

I do not sell consulting hours.I build commercial engines.

The intelligence · [GTM]lgy

The intelligence behind every engagement.

Every engagement is backed by GTMology, Gain Advisory's commercial intelligence engine. It reads thousands of signals about a company and its market, customers, competitors, and leadership, so every recommendation rests on evidence instead of assumptions.

The intelligence feed
Multi-source, verified, synthesized
News Press Hiring Jobs SEC Product Patents Funding Strategy Research Engagement Transcripts
Signal synthesis
Not one signal, but many, read together for the pressure underneath, until a specific thesis emerges about a company. Often a sharper read than the company has of itself.
Strategic account intelligence

Target lists scored to your ideal customer, refreshed as the market moves.

Competitive insight

How the field is positioning, and where the opening is.

Where Gain Advisory works

Deepest in financial markets.

Gain Advisory builds commercial engines for early- and growth-stage data, SaaS, AI, and fintech companies. Its deepest specialization is financial services.

Financial TechnologyCapital Markets TechnologyWealthTechRegTechMarket InfrastructureFinancial Data and AnalyticsGovernance and Compliance TechnologyInstitutional Investment Technology

Start your engine.

Grab 30 minutes and we will figure out, honestly, whether I can help and what that would look like.