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Engagement Mode: Coaching

When the Constraint Is at the Top, the Right Answer Is a Peer, Not a Playbook

Coaching engagements are built for CEOs and revenue leaders who are capable and have a team that can execute. What is missing is a credible thinking partner who has operated at this level before.

The hardest decisions in a revenue system do not have clean answers. Targeting strategy, hiring calls, board conversations, market moves that require a response before the picture is fully clear. Those decisions get better when they are made with a peer who has been in the same room before, not with a consultant presenting options from the outside.

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Fit Check

The Right Peer Is Not in the Building

Coaching is most useful when at least one of the following is true:

The board wants a narrative the leader is not yet sure of.

A missed quarter, a target the current model cannot reach, or a competitive shift that needs a response before the next board meeting. The direction has to be pressure-tested with someone who has built that kind of narrative before.

High-stakes decisions are being made in isolation.

Targeting, pricing, board positioning, partnership strategy. The decisions are consequential and the internal team does not have the operating experience to serve as a genuine sounding board. The leader is making calls without a peer in the room.

A senior revenue hire is not working, and the conversation cannot happen internally.

A CRO, VP of Sales, or Head of Marketing is underperforming. The question of whether the person is wrong, or whether the role was never going to work given the way the buyer actually decides, cannot be surfaced with the leadership team, the board, or the hire themselves. A peer outside the organization can help evaluate the diagnosis without political stakes in the answer.

The full picture cannot be safely put on the table internally.

The most consequential decisions involve the board, the leadership team, or the leader's own read on where the organization actually is. Those conversations cannot be fully surfaced inside the company without consequence. A peer who operates under full confidentiality and has no organizational stake creates the conditions for an honest working session that no internal relationship can replicate.

The blocker is not capability in the organization. It is the absence of a relationship where strategic direction can be pressure-tested by someone with the operating experience to push back meaningfully.

Coaching is not the right engagement when what is needed is structured external expertise to close a specific organizational gap, or embedded leadership with direct accountability for the revenue outcome. The GTM Maturity Assessment and a 30-minute consultation confirm the match.

The Engagement

Structured Working Sessions Tied to Live Business Challenges

Each coaching session is built around a specific business objective or challenge in front of you at that moment. Not a curriculum. Not a playbook handed over at the end of an engagement. A working session with a thinking partner who has operated at this level, focused on the decision or challenge that is most consequential right now.

The output of each session is not a deliverable. It is sharper thinking, a clearer decision, and an accountability structure that keeps execution aligned with intent between sessions.

Over the course of an engagement, the pattern of sessions produces something more durable: a leader who is making better decisions faster, with a documented operating discipline that does not depend on the coaching relationship to hold.

What a Typical Session Covers

A targeting decision that is not producing the results the model predicted, and the question of whether the hypothesis was wrong or the execution was. A hiring call where the instinct and the evidence are pointing in different directions. A board conversation that needs to be framed around the right problem before the wrong solution gets resourced. A market signal that may require a strategic recalibration or may be noise. These are the decisions that define the trajectory of the business.

They deserve a peer in the room.

What is discussed in a session stays in the session. No notes shared with the practice. No case studies written. No one else briefed. That is the condition that makes the most consequential conversations possible: the board conversation before the board conversation, the hiring call before the hire happens. What the client keeps across the engagement is a documented decision log and accountability structure, a working discipline that does not depend on the coaching relationship to hold, and clarity on where the constraint has shifted.

Who You'd Be Working With

Coaching sessions are led from the practice by a senior operator. Today that is Tony Larson. Three decades inside B2B software, through the full arc of founding, financing, scaling, turning around, and exiting. Co-founded Casenet LLC and served as senior executive through two successful acquisitions, scaling from startup to $50M annual revenue and 350 employees. Built all commercial organizations from the ground up: marketing, sales, implementation, and client success, as the CEO's primary business partner across strategy, product, and operations over an 18-year company lifecycle.

Background on LinkedIn →

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The Engagement Structure

How the Engagement Works

Engagement Structure

  • Twice-Monthly Executive Sessions. Two 90-minute one-on-one sessions focused on decision-making, strategic direction, and execution planning. Sessions are structured, not open-ended.
  • On-Demand Access. Responsive support via Slack or scheduled calls for time-sensitive issues, critical decisions, and real-time problem solving.
  • Session Summaries & Action Alignment. Concise documentation of key insights, decisions, and next steps to ensure clarity, continuity, and forward momentum.
  • Accountability & Execution Cadence. Ongoing alignment on priorities, commitments, and progress between sessions. Focus on ensuring decisions translate into action.

Decision Support & Strategic Insight

  • Situation-Based Advisory. Guidance tailored to your current business priorities, growth stage, and operating challenges.
  • High-Impact Decision Support. Structured input on high-impact decisions including go-to-market strategy, pricing, hiring, org design, and prioritization.
  • Diagnostic & Insight Development. Use of structured diagnostics and analytical tools to identify root causes, surface constraints, and uncover opportunities for acceleration.
  • Cross-Functional Advisory. Integrated perspective across sales, marketing, product, and client success to ensure alignment and avoid siloed execution.

Strategic Alignment & Stakeholder Readiness

  • Quarterly Strategic Review. Formal review of objectives, progress, and performance with recalibration of priorities based on results and market conditions.
  • Board & Stakeholder Preparation (as needed). Support for executive communication, board presentations, and alignment with investors or leadership teams.
  • Priority & Initiative Structuring. Assistance translating strategy into clear initiatives, sequencing, and resourcing decisions.

Engagements start at $2,500 per month and typically run two to four quarters. Scope, cadence, and duration are confirmed in the consultation.

Common Questions

Answers Before You Book

Coaching is for when the leader is capable and the team can execute, but the constraint is decision quality at the top. Consulting is for a specific, definable revenue gap requiring structured external expertise. Fractional Leadership is for when the CEO needs a revenue generation partner accountable for the number. The GTM Maturity Assessment and a 30-minute consultation confirm which mode fits.

Engagements are designed around the constraint you are working, not a fixed term. Most run for two to four quarters as the leader moves through a specific set of decisions. The engagement naturally concludes when the accountability structure no longer depends on the coaching relationship to hold.

The consultation is where match is confirmed. If coaching is not the right mode, the better answer may be Consulting, Fractional Leadership, or no engagement at all.

The coaching relationship operates under full confidentiality. What is discussed in a session stays in the session. No notes shared with the practice. No case studies written. No one else briefed. That is the condition that makes the most consequential conversations possible.

Coaching sessions are led from the practice by a senior operator. Today that is Tony Larson. The bar for an operator leading a coaching engagement is two decades of B2B software operating experience across the full lifecycle of founding, financing, scaling, turning around, and exiting.

The Methodology

Consistent Framework. Tailored to Your Situation.

Coaching engagements operate within The Enterprise Revenue Acceleration System (ERAS): the methodology that governs every BRCG engagement. The approach is consistent, hypothesize, validate with evidence, adjust, applied across the levers that actually drive revenue: targeting, pipeline, team, product, RevOps, and client value. The documented system it produces is tailored to your business, your stage, and the clients you are targeting.

See how the ERAS methodology is structured →

The Next Step

The Next Thirty Minutes

Thirty minutes. Your situation, the decision you are working, and a direct read on whether a standing coaching cadence is the right response.

  • The objective, decision, or constraint you are working right now. What it is, who it affects, why it has not resolved.
  • Whether a peer-cadence engagement actually fits. Or whether the better answer is consulting, fractional leadership, or no engagement at all.
  • If it fits, what the first 90 days look like. Session rhythm, scope of the working agreement, and how progress gets measured.

If you have not yet seen the diagnostic, the GTM Maturity Assessment identifies where the revenue system is structurally broken before an engagement begins. Useful context, not a gate on the conversation.

Schedule a Consultation Take the GTM Assessment if you haven't already →