Sales Coaching for B2B SaaS & AI Startups
Stop expecting reps to execute on tribal knowledge. We install the playbooks, process, and qualification standards your team needs, then coach them on live deals every week to build predictable revenue that scales.
Limit: 2 New Engagements / Month
“After a quarter of lackluster performance, I knew I needed a coach. I had been chasing deals that didn’t have a real chance at closing. Since working with Dustin, my quota attainment went from 80% last quarter to 238% this quarter, and I still have the pipeline to do it again. Huge transformation.”
Jesse Taylor · Enterprise Account Executive
MEDDPICC, Challenger, Sandler, SPIN, Command of the Message, ORDER, SPICED, SNAP, GAP, Solution Selling, Miller-Heiman, & other proven frameworks, distilled into one system your team can actually run
The Assumption Is The Problem
Most early-stage founders don't have a hiring problem. They have an infrastructure problem. Hired salespeople come in with strong resumes but they cannot replicate your founder authority, industry context, or personal network to close deals. Expecting them to replicate your intuition without a structured system is a 6-figure gamble.
The salesperson isn't the problem. The assumption is.
If the Assumption was true, the failure rate wouldn't look like this:
The Startup Genome Project studied 3,200 high-growth startups and found 74% of failures trace back to one cause: premature scaling, including hiring sales reps before the business was ready to support them.
PROVEN RESULTS
Revenue leaders and Account Executives who went from guessing to hitting quota, on the record.
Dustin has an encyclopedic knowledge of sales and is an engaging, accomplished, and extremely polished trainer and presenter. This is a killer combination when applied to supercharging a sales function.
Chris Riley · VP of Sales & ExecutiveDustin brings an energy and knowledge base that I have found unmatched anywhere else. I have never worked with someone that is so versatile in a sales organization. In a single day, he can go from sales leader to operations specialist to subject matter expert on just about everything. I would not only recommend Dustin, I would follow his leadership any day.
Josh Skinner · General ManagerDustin and his team helped our organization make major improvements. He rapidly identified the areas that would be most impactful to our business.
Chris Sams · Founder & Head of SalesThe training and coaching he put together was one of the best in my career, and as a former sales trainer, that's saying something.
Larry Boubel · Enterprise Account Executive & Former Sales TrainerDustin's exceptional leadership and strategic insight have been instrumental in my professional growth. His mentoring and coaching have significantly enhanced my effectiveness as an enterprise sales professional.
Mark Andrew · Enterprise Sales LeadBecause of his coaching and training, I went from not knowing what an objection even was to exceeding my quota every quarter.
Justin Driffill · Senior Account ExecutiveOur sales accelerated when we started working with Dustin. We ramped up outbound prospecting, filled the pipe, and started closing deals consistently. He holds you to a higher standard and teaches your team what it means to be a world-class sales professional.
Shawn Hughes · Founder & Head of SalesHe guides you towards success in the work that also makes you understand more about life. He is the perfect blend of analytical and intuitive that makes him understand basically everything about everything very quickly. I had so much fun working with Dustin, and I learned so much too.
Sam Dubin · Business Development LeaderDustin pulled our team out of a rut and re-lit my drive through encouragement, the right questions, and consistent level-up guidance. He didn’t just inspire me, he transformed our group into a high performing sales team. He is relentless about growth.
Brian Hall · Sales Development LeaderMax 2 New Engagements / Month
Repeatable Sales Infrastructure
Six core assets. One repeatable engine. We build the infrastructure beneath your team, then coach them on live deals every week so you can step back and scale the business.
We install a startup-specific sales process designed for early-stage B2B SaaS & AI. Everyone on your team follows a clear sequence with explicit exit criteria for every stage. No more guessing what to do next.
A binary qualification framework that replaces gut feel and rep optimism with verifiable buyer evidence. Your team learns to identify real deals early and stop wasting time on perpetual tire-kickers.
A structured interview framework that teaches your sales team how to uncover business pain to filter high intent buyers. Your team stops giving premature product demos to unqualified leads, increasing your conversion rate and decreasing your cycle time.
A documented deal closing plan, built with the buyer, detailing the steps in the purchase decision process. No more guessing how the deal will close. You know exactly what needs to happen, in what order, and who needs to be involved in the approval process.
Live, weekly group coaching where we review actual sales call recordings, roleplay objection handling, and inspect active pipeline. Reps sharpen their skills on real deals without draining your time.
A weekly operational rhythm that installs forecasting as a core competency into your team. Replaces weighted-pipeline fuzzy math with evidence-based criteria so you can walk into board meetings with total confidence.
Max 2 New Engagements / Month
Transparent Investment
From self-paced playbooks to hands-on sales leadership. Select the path that matches your current stage, team capacity, and growth goals.
$997
one-time
Includes: 5 field-tested playbooks, ready to install on your team's timeline:
Skip months of trial and error building from scratch.
$25,000
$10,000 install + $5,000/mo. for 3 months
Includes the Playbook Pack, plus 90 days of live installation and weekly coaching:
$75,000
2 days/ wk for 3 months
Includes the Startup Sales Engine, plus hands-on sales leadership advisory:
Only 1 slot available
Zero Heavy Lifting
No endless interviews or 50-page strategy documents.
Just 3 simple steps.
Weeks 0-2
We align on metrics, review 2–5 sales call recordings, and inspect existing collateral. Then we run two 90-minute live team sessions to install the Start-to-Signature method, TRACK qualification, and High-Def Discovery. Your team walks away with a unified sales motion and shared language.
Weeks 3–12
We run 10 weekly Film Room group coaching calls directly with your sales team to review call recordings, anchor concepts, and master deal strategy. Concurrently, we run bi-monthly 1:1 founder advisory calls to review metrics, tackle scaling challenges, discuss GTM decisions.
Week 12+
The knowledge, skills, and competencies we installed hold permanently, because your team is executing their own proven system for repeatable success. Your sales team operates as a predictable engine and becomes a talent magnet for top reps that want to join a winning organization.
Max 2 New Engagements / Month
Hi, I'm Dustin Gransberry, The Startup Sales Coach
Most advisors push pitch decks that are quickly forgotten and big-company playbooks that don't work at your stage. I install a foundation for scale, clear definitions, sales playbooks, close plans, forecasting, and leadership advisory, and we reinforce execution through coaching until best practices become second nature.
Going from zero-to-one is a unique challenge. And one I've obsessed over for the last 17+ years. I've sat in every seat of a revenue org from top performing AE, manager, RevOps, enablement, and 3x VP sales. I've trained hundreds of top performers, built sales infrastructure for over a dozen companies, closed Fortune 100 deals, and helped founders raise millions in VC-funding.
I care about salespeople and the entrepreneurs brave enough to take a shot. And I'm done watching great products die because founders were pressured to scale before they were ready. Having the right foundation makes all the difference. Let's build it together.
If your team does not achieve measurable gains in win rate, pipeline velocity, and deal predictability within 90 days of installation, we work with you at no additional cost until they do.
Before You Commit
B2B and AI startups, Seed to Series A, usually with 2 to 10 salespeople. If you are running a highly transactional, one-call-close business or an online checkout model, this isn't for you.
Most training programs lack the reinforcement mechanism (coaching) that makes the method stick. So, your sales team defaults to ineffective behaviors, burns leads, and fills your pipeline with trash. Not only that, most training programs are too heavy for your stage of company. You need something that is specifically designed to work for a startup. Your sales team doesn't have founder-level gravitas, your domain knowledge, or the luxury of a known brand. They will struggle unless they have a method that is designed for the selling situations they find themselves in. We coach your team on live deals every week until the method shows up in the numbers.
No. Coaching is a distinct function from management. We install the training and coaching layer your team is missing, we don't run your sales org. However, we support you and your sales leader to generate more results, more quickly, with less stress.
Both, in sequence. We train the foundation first, then coach your team weekly until they master it.
That's great. You are ahead of the curve. We build on what's already working. Most startups have fragments of a sales process and lack essential disciplines. We fill the gaps and give everyone one shared language and method to execute.
The Startup Sales Engine installs training and coaching. Fractional Leadership adds advisory in areas like GTM strategy, comp design, and rules of engagement on top, for founders who need more than a system installed or who want a bridge to a full time Head of/VP Sales.
Most teams see the shift in qualification and forecasting accuracy within the first few weeks. Behavior change on live deals compounds over the full 90 days. At the beginning of the engagement we select KPIs to measure performance. My view is that if the training and coaching is only valuable if it produces a measurable lift in your numbers.
Book a 30 minute alignment call. On the call, we'll discuss your current goals and challenges. If there's a fit, I'll walk you through how we work together. If not, I'll recommend other options, either way you leave with more clarity on what to do.
"Since working with Dustin, my quota attainment went from 80% last quarter to 238% this quarter."
Jesse Taylor, Enterprise Account Executive
"Dustin has an encyclopedic knowledge of sales, a killer combination for supercharging revenue."
Chris Riley, VP of Sales
"He helped us build a world class team."
Shawn Hughes, Founder & Head of Sales
"An energy and knowledge base unmatched anywhere else. Highly recommended."
Josh Skinner, General Manager
P.S. Because we invest heavily in your team's success, we only take on a maximum of 2 new engagements per month. If you want a pipeline you can actually trust, a team that runs deals without you, and a sales system that turns inconsistent performance into predictable revenue, book a call now.