By Cathy Garland, Senior Consultant, Value Based, Inc. | Former SaaS COO and Sales & Marketing Executive

Choosing a sales coaching partner can seem pretty straightforward. Find a company with a proven methodology. Look at its client list. Schedule a demo. Compare programs and pricing. Make a decision.

But if you're responsible for revenue at a SaaS company, you're choosing much more than a training program. You're bringing in someone who will influence how your team talks to prospects, how your managers coach, how opportunities move through the pipeline, and ultimately how your company communicates value.

So I think the better question is this: Who can help us build a sales organization that sells according to our values, gets really good at proven sales practices, and produces results we can measure and sustain?

Here are the things I'd look for.

1. Choose Someone Who Understands Why SaaS Sales Is Different

SaaS is incredibly competitive, and one of the biggest mistakes a sales team can make is building its strategy around features and benefits. Why? Because features aren't much of a moat.

I learned this firsthand selling a learning management system to corporations and higher education. A prospect would see a feature in a competitor's demo, and suddenly that feature was important. Then they'd come to us asking whether we had it. Sometimes we had something better. Sometimes we had to explain why they didn't really need it. And sometimes the answer was, “Yes, we're building that right now. Let me show it to you next week.”

It became a constant race. There were even times when something a prospect saw in a competitor's demo helped drive our R&D priorities. That's the nature of SaaS. You may have a capability today that none of your competitors can match, and it may absolutely help you win a deal. But give the market a little time. Competitors watch each other. Products evolve. Development teams release new functionality. AI is speeding that cycle up even more. The feature that sets you apart today may be standard across your category tomorrow.

That doesn't mean features and benefits don't matter. They do. They're just not enough to build a lasting sales advantage.

That became very clear when Jim Allen trained my sales team to stop leading with features and benefits and start selling value. Instead of showing prospects everything our software could do, we learned to uncover the problem they were actually trying to solve and connect our solution to what mattered to them.

It changed the conversation, but it also changed our willingness to discount. When you're competing feature for feature, it's easy to feel as though you have to lower the price because you're missing something on someone's wish list. When the conversation is about the value of solving the buyer's actual problem, price sits in a very different context.

Your salespeople need to know how to have that conversation. What problem is the buyer trying to solve? Why does it matter? What is it costing them now? What changes if they solve it? And is that change worth the investment, disruption, implementation, and risk involved? That's a very different conversation from walking through a feature list.

It also helps to have a coaching partner who understands SaaS from the inside. Your sales process may involve SDRs, AEs, sales engineers, implementation teams, customer success, executives, and several stakeholders on the buyer's side. Closing the initial deal isn't the end of the story either. Adoption, renewal, expansion, and recurring revenue matter too.

Your coaching partner doesn't have to know your exact software, but they should understand the world your salespeople work in and why selling value instead of relying on features is so important in SaaS.

2. Start With Your Values, Not Someone Else's Script

There are proven best practices in sales, but there isn't one script, process, or sales personality that should be dropped into every company unchanged. Your values matter. So do your customers, contract size, sales cycle, competitors, culture, and the way your buyers actually make decisions.

A good partner should spend some time learning those things before telling you what needs to change. What matters to you as an organization? How do you want prospects to experience your sales team? Where are you losing deals? What's already working? Where is the inconsistency? What does your buyer's journey actually look like?

This matters even more with consultative selling because authenticity matters. You don't want good salespeople suddenly sounding as though they've memorized somebody else's script. The goal isn't to make your salespeople sound like your sales coaching company. It's to help them become better representatives of your company.

3. Connect Sales Enablement to the KPIs That Actually Matter

“Your team loved the training” is nice to hear, but it isn't a business result.

I've been on the executive side of that equation. At some point, you need to know whether anything is actually changing. Are we converting more opportunities? Is the sales cycle getting shorter? Are we discounting less? Are our people getting better at the work?

In our case, one of the most obvious problems was the sheer number of demos we were doing. A prospect might go through four to six demos as we worked our way up the organization. My salespeople were doing more than 20 demos a week, and some were literally losing their voices.

After all that work, the deal could still implode when it finally reached the CTO. We discovered that the software integrations most important to the CTO weren't always the ones the prospect had identified as most important. They weren't always the ones we assumed would matter most either. We could spend months demonstrating the LMS, answering feature questions, and moving a deal through the organization only to discover late in the process that the CTO had an integration requirement that could stop the whole thing.

That wasn't simply a training problem. It was a sales-process problem. So we changed the process, and eventually those 20-plus demos a week became two. I'll come back to how we did that, because the bigger point here is that we had something concrete to measure.

Before you start an engagement, you and your coaching partner should agree on the problem you're trying to solve and what you'll measure to know whether things are improving. Those Key Performance Indicators (KPIs) will depend on your goals. You might look at lead-to-opportunity conversion, close rates, sales cycle length, pipeline velocity, average contract value, discounting and margin, new-logo revenue, expansion revenue, ramp time, forecast accuracy, or something else entirely. What's important is having a baseline before you begin.

Nobody should pretend sales coaching happens in a vacuum either. Markets change. Products change. Pricing changes. Competitors change. I'd be wary of anyone who wants to take credit for every revenue increase that happens after training.

Instead, good Sales Enablement should connect what people are learning to what they're actually doing, then check whether those changes show up in the numbers that matter. Leaders should be able to answer two questions: Are our people getting better at selling? And are we seeing that improvement in our sales performance?

4. Look Beyond Training to Mentoring, Coaching, and Practice

Knowing what to do isn't the same as being able to do it with a real prospect. I've watched salespeople know all the right questions to ask and still fall back into what's comfortable when the pressure is on. In software sales, what's comfortable is often the demo. It's much easier to start showing someone what the product can do than to slow down long enough to understand why they might need it.

A salesperson can understand discovery and still conduct a poor discovery call. They can explain exactly how they should handle an objection and fall right back into old habits when a prospect raises one. They can know they shouldn't rush into a demo and still find themselves sharing their screen five minutes into the conversation.

That's why sales development has to go beyond teaching content. Look for mentoring, coaching, role-playing, observation, feedback, reinforcement, and lots of practice. People need room to try something new, get it wrong, receive feedback, try it again, and keep working until the new behavior starts to feel natural.

Instead of asking, “Did our people complete the training?” ask, “Can they actually do it?” That's a much higher bar, but it's also what you really need.

5. Look for Certification Based on Proficiency, Not Attendance

This becomes especially important if the coaching company offers certification. Ask what “certified” actually means. Did someone attend the required sessions, watch the videos, and pass a multiple-choice test? Or did that person actually demonstrate the ability to use the sales practices they were taught?

There's nothing wrong with testing knowledge. You have to understand the principles before you can apply them. But knowing and doing aren't the same thing.

Certification should mean something. It should give the salesperson a clear standard to work toward and give managers a better picture of where more coaching is needed. If you're making a significant investment in Sales Enablement, you don't just want proof that your people were exposed to a methodology. You want to know they can use it.

6. Choose a Partner Who Plans to Stay Long Enough to Make It Stick

One of the biggest problems with traditional sales training isn't always the training itself. It's what happens afterward. Everyone leaves energized, new terminology starts popping up in meetings, and managers reference the training for a few weeks.

Then the quarter gets busy. People are under pressure to hit their numbers, and little by little, old habits come back. Changing behavior takes time.

So when you're considering a coaching partner, ask what happens three, six, or even twelve months after the initial training. Is there ongoing coaching? Role-playing? Reinforcement? Competency assessment? Are managers involved? Is there a plan for helping these practices become the normal way your team sells?

A two-day workshop can introduce an idea, but it usually can't change a sales culture. You're looking for a progression from learning to practice, application, measurement, coaching, certification, and eventually sustained proficiency.

7. But Don't Choose a Partner Who Makes You Dependent on Them

There's a balance here. You want a partner who's willing to stay long enough to help the changes stick, but you don't want to call that partner every time you hire a new salesperson. One question I'd ask is, “How are you going to help us eventually own this ourselves?”

At some point, Sales Enablement should become an internal capability. As an operator, this is where I'd start thinking beyond the people on the sales team today. People leave. Companies grow. Roles change. Six months after the consultants are gone, you're going to hire someone new. If the methodology walked out the door with the consultant, what exactly did you buy?

A strong approach may include developing and certifying one of your own leaders to onboard new hires, reinforce the methodology, conduct role-playing, mentor and coach the team, and maintain consistency as the company grows.

Think about what happens when you hire five new salespeople next year. Do you have to buy another external training engagement to get them up to speed? Or do you now have people and systems inside your own company that can develop those five salespeople to the same standard?

The first keeps you dependent on a vendor. The second gives you an organizational asset. A good coaching partner should want to leave you stronger, not permanently dependent on them.

8. Make Sure Your Sales Managers Are Part of the Equation

Outside consultants can't carry this forever. At some point, your managers have to own it. They're the ones conducting one-on-ones, reviewing opportunities, looking at pipeline, listening to calls, and helping salespeople work through real situations. When the pressure is on, what the manager reinforces is probably going to win.

So ask how the coaching partner will equip your managers. Do they know what good performance looks like? Do they have a shared language and clear competencies? Can they spot where an individual salesperson needs help? Do they know how to coach someone toward improvement instead of simply telling them what to do?

That's when sales coaching starts becoming part of how your company operates instead of something your company did once.

9. Find Someone Willing to Tell You When Training Isn't the Problem

Sometimes the problem isn't your salespeople. That's exactly what we discovered with all those LMS demos.

After Jim trained our team to sell value instead of features and benefits, we were having better sales conversations. But I also realized our sales process was working against us, so I reorganized the team.

I moved some of my toughest salespeople to the very front of the process. They weren't necessarily the people I wanted doing the deeper consultative work later in the sale, but they were very good at qualifying opportunities and moving conversations forward.

When someone called asking, “Do you have this feature? Do you have that feature?” we stopped launching into a product presentation. The response became essentially, “I'm confident we do, but let's make sure. Which demo works better for you, Tuesday morning at 10 or Thursday afternoon at 1?” We funneled prospects into two scheduled demos a week. Period.

But we made another change that mattered even more. Early in the conversation, we'd say something along the lines of, “In our experience, no enterprise software purchase goes through without making sure it integrates with the systems you already depend on. So let's schedule a conversation with our VP of Sales and CTO and bring your CTO into it too.”

That one request told us a tremendous amount. If the prospect could get their CTO into the conversation, we could identify and work through the biggest potential technical obstacle before investing months in the sales process. If the response was, “We're not quite at that point yet,” we learned something equally important. The person we were talking to probably didn't yet have the authority or internal support to make the purchase, no matter how many demos we gave them.

We stopped spending enormous amounts of time selling to people who weren't in a position to buy, and the numbers changed. We went from more than 20 demos a week to two. When we got the right decision-makers into the process early, our close rate rose substantially. Sales cycles that could stretch to roughly two years dropped to less than three months when the new process worked as intended. And because our team was selling the value of solving the client's problem instead of trying to compensate for every missing feature, we stopped relying on discounting to win deals.

Jim's training mattered. It changed how our team thought about selling. But training wasn't the only thing that needed to change. Once we understood the principles, we also had to build a sales process around them.

That's why I don't believe every sales problem should automatically lead to more sales training. Maybe it's your process or your positioning. Maybe you're qualifying the wrong opportunities. Marketing and Sales aren't handing leads off well. Managers are reinforcing the wrong behaviors. Your incentive structure may even be rewarding something you don't actually want.

A good sales consultant should be willing to find that out. That's why diagnosis should come before training. Look at the people, practices, processes, KPIs, and sales environment first. Then decide what needs to change.

If every problem somehow leads to the exact same prepackaged training program, you probably haven't hired a consultant. You've bought a product. I'd rather work with someone who's willing to ask hard questions, challenge our assumptions, and occasionally tell us that the solution isn't what we expected it to be.

So, How Should a SaaS VP Choose a Sales Coaching Partner?

I wouldn't make the decision based primarily on how many modules are in the program, how impressive the learning platform looks, how charismatic the trainer is, or how many recognizable logos are on the website.

I'd look for someone who understands SaaS and knows why features and benefits alone aren't enough in a market that changes this quickly. I'd want them to understand our values before trying to change how our people sell, diagnose before prescribing, and adapt proven best practices to the way our company actually works.

I'd also want us to agree on meaningful KPIs from the beginning. Then I'd want to see our people developed through training, mentoring, coaching, role-playing, and real practice. And if certification is part of the program, it should mean they can actually demonstrate what they've learned.

Finally, I'd ask two questions that may sound contradictory: Will you stay with us long enough to make this stick? And will you equip us well enough that eventually we don't need you to?

The answers will tell you a lot. Because the goal isn't really to buy sales training. It's to build a sales organization that knows how to discover what matters to a buyer, communicate meaningful value, and consistently put proven sales practices into action.

That's an organizational capability worth investing in.

About the Author

Cathy Garland is a Senior Consultant with Value Based, Inc. and former COO and sales and marketing executive of an award-winning SaaS learning management system. After more than 20 years serving software/SaaS and higher education organizations, she now works with Value Based clients to strengthen sales strategy, Sales Enablement, and value-based selling practices.

How Should a SaaS VP Choose a Sales Coaching Partner?

How Should a SaaS VP Choose a Sales Coaching Partner?