ENTERPRISE SALES COACHING
I coach founders and reps inside live opportunities to uncover what’s blocking the decision, strengthen the business case, equip the champion, and determine what must happen next.
This isn’t generic sales training. It’s deal-specific coaching for high-value opportunities where a small number of decisions can materially affect revenue.
Bring Me The Deal That’s Not Moving
The people who find you aren’t the ones who fund you.
Your champion may believe in the value. But they still have to explain it to the executives who own the budget, risk, and decision.
Our job is to equip them to make that case when we’re not in the room.
Until an executive owns the decision, it’s interest, not a deal.
Four conditions must form before buyer interest becomes a defensible decision
1. A named executive owns the decision. Someone with authority accepts accountability for the business outcome and can mobilize the people required to approve and fund it.
2. The business case can withstand scrutiny. The champion can connect the investment to revenue, cost, risk, or execution outcomes and explain the consequence of waiting.
3. The buyer believes the change can be executed. There’s a credible go-live plan covering actions, owners, dates, adoption, and the path to the promised business outcome.
4. There’s enough urgency and internal alignment to act. The key stakeholders agree on why the initiative matters now and why it should win against competing priorities.
When one of these conditions is missing, deals tend to drift.
How I help create decision movement
Diagnose what’s missing. We pressure-test the four conditions behind a defensible decision: executive ownership, business-case strength, execution confidence, and enough urgency and alignment to act.
Build the internal case. We translate product value into an executive-ready argument tied to revenue, cost, risk, strategic priority, and the consequence of waiting.
Equip the people carrying the decision. We determine whether a viable champion exists, give them language and tools that can travel internally, and identify the next customer action required to show whether the decision is truly progressing.
Discuss a Live Deal
Meet Mark
I’m Mark Phinick, founder of Let’s Make It Rain and a B2B sales and deal coach with decades of experience in enterprise technology sales and leadership.
My career has included senior sales leadership roles at IBM and HCL, along with work across startups, public companies, acquisitions, cybersecurity, AI, IT operations, software, and services.
I’ve seen strong solutions lose because buyer interest never became a business case executives could approve and act on. I’ve also helped teams overcome those barriers, which shaped how I approach enterprise deals today.
Today, I coach founders, sales leaders, and sellers inside live opportunities. Together, we identify what’s blocking the decision, strengthen the business case, equip the people carrying it internally, and determine what the buyer must do next.
I’m also the author of When Deals Go Quiet: Navigating the Silence Between Interest and Decision in Enterprise Sales.
What Clients Say
“After one call with Mark, I learned more than I had from several other conversations. He has a rare ability to quickly zone in on the real issue, give direct, no-sugar-coated advice, and make the time immediately valuable. It was one of the best calls I’ve had in a long time. I’d recommend giving Mark an hour of your time. Worth every penny.”
Josh Van Dress, Founder & CEO
Quintic Labs
“Mark helped me turn a pilot into Experio’s first paid customer. He pressure-tested the offer, sharpened the business case, and coached me through the buyer conversation and follow-up. That win directly triggered a VC investment. Mark doesn’t give generic sales advice. He gets inside live deals and helps founders turn momentum into revenue.”
Daniel Cohen-Dumani, Founder & CEO
Experio Labs
“Mark is an exceptional sales coach. His approach to deal-making is practical and grounded in how enterprise business decisions actually happen. With his help, I’ve taken my sales craft to another level, integrated AI into my process to work smarter, and recently closed one of the biggest deals of my career. He is excellent at helping translate complex challenges and solutions into outcomes that executives can actually act on. Highly recommended working with Mark!”
Carylanne Wolfington, Account Executive
Google Cloud Security
“What I love most about working with Mark is his enthusiasm and his intense desire to create great outcomes for his clients. Particularly with early-stage technologies, Mark is very talented in helping clarify why and how that technology can really propel the client to what they’re trying to accomplish.”
Anthony Aurigemma, VP Global Alliances Palo Alto Networks
“When I started working with Mark, sales felt like a mystery and, honestly, a little intimidating. He helped me translate a complex consulting offer into language executives could quickly understand, improve my outreach, and approach real opportunities with more structure and confidence. His coaching was practical enough to apply immediately. In one LinkedIn test, his approach generated 105 new connections versus 35 with mine. More importantly, he taught me how to connect my work to business outcomes, ask better questions, and end conversations with a clear next step. I got exactly the intellectual ROI I was looking for and a much stronger foundation for growing 3Fold.”
Jason Zimmerman, Founder & CEO
3Fold Collective
“Mark brought valuable enterprise sales experience to Aiden at an important stage of our growth. He helped us adopt MEDDPICC as a more disciplined sales framework, sharpen our thinking around complex enterprise sales cycles, and better connect Aiden’s technical capabilities to customer outcomes, executive priorities, and the business case required to move opportunities forward. I personally benefited from his coaching and perspective, and Aiden came away with several practical practices and frameworks that continue to influence how we sell into large organizations.”
Josh Aaron, CEO
Aiden Technologies
Sales Coach vs. Sales Trainer: Which Do You Need?
Sales training helps a team build common skills, language, and process. Deal coaching helps a founder or rep apply those skills inside a live opportunity where revenue is at risk.
I don’t run generic training programs. I work with founders, sales leaders, and sellers on the deal in front of them, diagnosing what’s blocking the decision, strengthening the business case, and equipping the champion to move it forward.
You probably need sales training when…
A group of reps needs the same foundational skills
You’re rolling out a methodology across the company
New hires need structured onboarding
Managers need a repeatable curriculum
You’re planning an SKO or workshop
You probably need deal coaching when…
An important opportunity isn’t moving
The champion can’t make the case internally
Executive ownership is missing
The business case won’t withstand scrutiny
The close date reflects the seller’s forecast, not the buyer’s process
Training improves general capability.
Deal coaching applies that capability where revenue is currently at risk.
Bring me the deal that’s not moving.
