Sales Coaching for Agency Owners: What It Should Fix

Many agency owners close well once they're in a meeting with a good buyer. What they're short on is those meetings, so a sales program promising to help them close more deals is aimed at a problem they don't have.

Sales coaching earns its fee on two other problems: good meetings that end in a lost proposal, and deals that close only when the founder is on the call.

Key Takeaways

• Sales coaching for agency owners should cover the path from first call to signed proposal: how you describe the firm, discovery, scope and price, the proposal, follow-up and a weekly review of open deals.
• Too few meetings is a positioning or pipeline problem. Coaching helps when good meetings don't close, or when only the founder can close them.
• A good coach works on the deals you have open: what discovery found, when the buyer first heard a price, and what the next follow-up adds.
• Judge coaching by your pipeline and your calendar, starting with your close rate on deals the founder didn't lead.

What should sales coaching for agency owners cover?

Sales coaching for agency owners is one-on-one work with an experienced operator on how the owner, and later the team, wins new clients, using the deals the firm has open right now. It should cover the whole path from first call to signed proposal: how you describe the firm on the call, discovery, scope and price, the proposal, the follow-up, and a weekly review of every open deal.

Much of what's published as sales coaching is written for a sales manager coaching a team of reps, with role-play and call feedback. At a founder-led agency, the person being coached is usually also the person selling. In SparkToro's 2025 agency survey, 70% of agencies had no staff dedicated to sales full time.

That changes where the coaching starts. A rep is asked to sell inside a process somebody else built. An owner is building the process while running it, so the coaching has to reach who you sell to and how the price gets set before it gets to technique on the call.

Do you need sales coaching, training or more leads?

Before you buy anything, find out how many good meetings you get and how many of them you win. Too few meetings calls for positioning or pipeline work, while meetings that don't close and deals only the founder can close are where sales coaching helps.

You get too few good meetings and win most of the ones you get. Your trouble is getting in front of buyers. Whether you reach buyers you can help, and whether they have a reason to take the call, are positioning and pipeline questions.

You get good meetings and lose them at the proposal or on price. The work is discovery, the proposal and the point where the price first comes up. If buyers mostly compare you on price, check your positioning too, because that's a sign they can't tell you apart from the other agencies on their list.

Deals close only when you're on the call. Some of that is skill you've earned, and some is context your team has never seen: which question opens up a vague brief, or which work sample matters to this buyer. A documented agency sales process moves that context out of your head. Build one before you make your first sales hire.

Tim Kilroy describes the usual reflex in his Agency Sales Playbook: "Most agency owners are convinced they've got a sales problem, so they go shopping for a fix."

When an owner asks me whether pipeline work is just sales training, my answer is the one on Schmidt Consulting Group's agency pipeline page: sales training assumes the way you sell is already sound and the team needs better execution. It has a place once that's true.

What happens in a good sales coaching session?

A good session starts from a deal you have open this week. You go through what discovery found, how the scope and price were set, and what the next follow-up will say, and you leave knowing the next step on that deal.

Reviewing a live deal

A live deal gives the coach evidence to work from: the notes from the first call, the brief, the proposal draft and the email thread. In Advisory, the weekly engagement at Schmidt Consulting Group, you bring the live deal and we work the pricing and the scope before the proposal goes out.

Bring the losses as well. The deals that stalled, the work you discounted to get, and the ones that closed only because you jumped in tell you what keeps going wrong.

Treating discovery as diagnosis

Say a prospect asks for a new website. The reason behind the request could be weak positioning, a conversion problem, technology their team no longer wants to maintain, a launch with a date attached, or an executive who's embarrassed to send people to the current site. Each of those is a different engagement at a different price.

A coach checks whether your discovery found out which one it is. Your notes should say what the client is trying to change, why it matters now, who else gets a vote, and what result would justify the spend.

Naming the price before the proposal

Blair Enns, author of Pricing Creativity and The Win Without Pitching Manifesto, has a rule I treat as non-negotiable: say a price before you show a price. Tell the buyer a price range before you write the proposal, so you hear any price objection before you've done the work. Say the high end of the range first. My guide to agency pricing models covers anchoring the range and building three options.

Scope belongs in the same conversation. The best time to discuss scope boundaries is before the contract is signed, so a coach will ask what's included, what's excluded and who approves a change. What scope creep is and how to prevent it covers setting those boundaries with a client.

Following up with something useful

After the proposal, each follow-up needs a reason beyond "you didn't reply." Add something useful or ask a specific question, and reply inside the original thread so the buyer keeps the context. These proposal follow-up email samples lay out four emails over two weeks.

A coach will also ask whether you have a date for the buyer's answer.

Can a founder who hates selling get good at it?

Yes. At an agency, the seller's job on a first call is diagnosis, which has more in common with client work than with pitching.

What makes it stick is a weekly rhythm. In Advisory, every session opens with last week's priority and whether it got done. A sales priority can be small, like giving a price range on the next discovery call, and when it doesn't happen, we work out what got in the way.

Selling well at an agency takes a few skills, like discovery and naming a price, and a few practices, like the weekly deal review. Dustin Rea, Founder and CEO of Red Hook, put it in those terms: "Kurt showed me the skills and practices I was missing."

What are your options for agency sales help?

Agency sales help comes in four kinds: generic sales training, agency-specific sales methods, agency coaches, and one-on-one advice from an operator. Pick the kind that matches your problem: too few meetings, meetings that don't close, or deals only the founder can close.

If you're comparing coaches across positioning, pricing and operations as well as sales, my guide on how to choose an agency growth coach sorts the best-known names by the problem each one works on.

How much does sales coaching cost?

The cost of sales coaching depends on how often you meet, whether you share the coach with a group, whether your live deals get reviewed, and how long you commit. Schmidt Consulting Group doesn't publish prices, and you get the number on the first call, before any commitment.

How much of the work the coach takes on matters as much as how often you meet. My comparison of an agency coach, consultant and fractional CMO covers how those three tend to price against each other.

Commitment varies too: Mentorship and Advisory both run month to month, and there's no paid diagnostic or paid discovery phase before either one starts.

Before you compare fees, put a rough cost on the problem: the good deals that died at the proposal last quarter, the evenings you spent rewriting proposals, and the deals that waited for a free slot on your calendar.

Any quote you get should separate the coach's work from the work your team will carry. My guide to what agency growth services cost covers comparing quotes line by line before you compare the fee.

How do you know sales coaching is working?

Judge it by your pipeline and your calendar. Coaching that works should bring more deals that close without you rescuing them, and more first conversations with buyers you want when pipeline work is part of it.

These numbers from my agency sales process guide tell you whether it's working:

• The share of discovery calls with a buyer who fits the clients you serve and has a reason to buy now.
• Close rate by lead source.
• Close rate on deals the founder didn't lead.
• How often proposals get revised before anyone approves them.

A rising close rate on deals you didn't lead can also mean the lead mix shifted or the deals got smaller, so check both before you credit the coaching. Give the numbers longer than a quarter, until you're reading a pattern.

Early signs are small and specific: someone other than you books a first meeting, or a proposal goes out while you're on a plane. If you're mostly collecting frameworks and slide decks, ask what has changed in your pipeline since the start.

How does Kurt Schmidt coach agency owners on sales?

I coach agency owners on sales through two one-on-one engagements, Mentorship and Advisory. I'm Kurt Schmidt. I was President and Partner at Foundry, a Minneapolis custom software and digital product agency, and grew it from 3 people to about 50. Foundry made the Inc. 5000 in 2020 and 2021, and I've advised more than 150 agencies.

Mentorship is twice-monthly counsel: two video sessions a month with the agenda set by you, and questions answered within one business day in between.

Advisory is a written plan, one priority at a time, and a weekly session with deal reviews when a deal is live. In both, you and your team do the work.

Bring one deal you have open this week. We'll talk it through, and you'll know by the end whether coaching fits and what it costs. Book a Call.