How to Choose a Sales Training Provider

When sellers lack the skills to confidently win a complex B2B sale, they find themselves stuck in a confidence chasm. They need training to help them bridge the gap. Sales leaders, meanwhile, face a confidence chasm of their own. When it comes to picking a provider, proliferating tools and solutions mean they face more options, more AI-hype marketing, and less clarity around what actually drives behavior change. A sales training request for proposal (a sales training RFP) should solve this problem by evaluating providers on strategic alignment, methodology rigor, AI and technology use, coaching/systems integration, and scale — not price, certifications, or feature lists.

If your old RFP format doesn’t evaluate across these categories, it’s time for a change.  

Why does your RFP need to change?

The sales training market totals $2.2B in North America alone, according to Training Industry, and buyers now research vendors with more sources and more AI assistance than ever. Gartner found B2B buyers consult an average of seven information sources per purchase, and 45% use generative AI to research vendors. An RFP built on a decade-old checklist won’t surface what actually predicts a good fit. Every provider claims some AI capability, and few can tell you whether that capability actually drives behavior change.  

Sales leaders must know early whether a sales training provider or even a sales tool is a good fit. For that, they’ll need to build an RFP around questions that investigate strategic and buyer alignment. 

What should your RFP ask about strategic and buyer alignment? 

Does the training connect to your actual business strategy?

For a sales training initiative to have any teeth, it needs support from the highest levels of company leadership. The fastest route to that support is ensuring up front that the training connects directly to your business strategy. When executives evaluate their strategy, they should be able to easily see how sales training supports their goals. For instance, if growing through expansion is a key strategic initiative for your company, the ideal sales training provider will offer programming, skill-building tools, and manager support aligned with that initiative. This is the step that keeps sales training from feeling like another thing to manage. With the right partner, sales training should support strategic business priorities from many angles.

Does the training support how your customers buy today?

The buying process is changing fast. Buyers now arrive more informed, with a shorter list of potential partners, and looking for information to help them narrow down the list. A 6Sense survey found that 94% of buying groups now arrive with their shortlist of vendors already ranked before the seller even enters the room, and they used an LLM to build that list. What’s more, the vendor sitting at the top of that shortlist wins eight out of 10 times. To create the kind of standout buyer experience that drives buyer loyalty, sellers need to bring unique insight that can’t be surfaced by AI and prove their value as a consultative partner.  

Beyond that, sales training that’s aligned with a customer’s buying process is simply good for the success of the entire sales organization. For example, a sales methodology that helps sellers identify buyer signals and predict forward movement improves forecast accuracy. Asking how training helps sellers prepare for modern, AI-enabled sales experiences should be top of the list when evaluating a sales training provider. 

Does the provider have relevant industry expertise and experience at your scale?

Relevance matters in sales training, both at the individual level and for the entire organization. The sales trainers, practice tools, and scenarios you put in front of skeptical sellers must be customized to their industry. Likewise, the sales training must be able to support your company’s size and stage of growth. Smaller, younger startups need different support than long-established Fortune 500 companies. Consider factors like the ability to scale globally, the size of the facilitation bench, and the expertise of those facilitators when drafting a sales training RFP. 

What should your RFP ask about methodology and proof? 

Not all sales methodologies ground themselves in behavioral science, research-backed behaviors, or real selling scenarios. Asking how sellers iteratively learn outside the classroom is one way to assess whether a program is truly structured to learn, or just presented as content. Pressing for proof of actual behavior change is another.

• Does the provider offer objective skill/competency assessment before training starts? 
• Is the methodology teachable and coachable, or just content? 
• What’s their evidence that it changes behavior, not just completion rates? 

What should your RFP ask about AI and technology?

Most sales training RFPs ask "does this include AI?" That's the wrong question because nearly every provider will say yes. The better question is whether AI orchestrates behavior change across the full arc of development, or whether it's a single feature bolted onto an old model. 

Ask providers to show, not tell, across five things: 

• Orchestration, not a point solution. Does the provider's AI connect performance data, learning, coaching, and reinforcement into one system that tells sellers and managers what to do next, or does it live in an isolated tool with its own separate dashboard?
• Grounded in methodology and behavioral science, not generic content. Is the AI defining and reinforcing specific, observable selling behaviors tied to a proven methodology, or improvising its own standards?
• Practice that connects to what comes next. If the provider offers AI roleplay, does performance in practice feed into what a seller works on next and what a manager coaches, or does it end at a completion score in an isolated dashboard? 
• Reinforcement in the actual flow of work. Does AI show up where sellers already work (CRM, Slack, Teams), or does it require sellers to log into a separate platform to get value?
• Connects to what you already run, not a rip-and-replace. Does the solution integrate with your existing CRM, conversation intelligence, and enablement stack, or does it ask you to start over?

The goal is guided action and personalized development that changes behavior for good, not more data, more dashboards, or a one-size-fits-all AI layer. 

What should your RFP ask about coaching and systems integration?

Does the provider train managers to coach the behaviors, not just train reps to perform them? 

Coaching is fundamentally different from performance management, and the most robust sales training programs acknowledge this difference. First, because the involvement of prepared coaches helps reinforce behavior among frontline sellers at the individual level. The individual behaviors that add up to a successful sales motion develop over time, and managers should be prepared to address and correct individual gaps as they play out after training. Second, because good coaching improves seller outcomes, and poor coaching is more detrimental to performance than no coaching at all. Simply helping coaches get better at their work, regardless of which methodology they’re teaching, will improve organizational outcomes.  

What should your RFP ask about scale and sustainment? 

Finding a provider that can scale alongside your business means pressing on questions that get at the success of its sustainment strategies. The two go hand in hand because, after you’ve rolled out a new sales training program, sustainment is what drives continued growth and success. Whether you want to scale across business units or even bring a new sales training methodology to a global organization, the right provider will be able to answer how they deliver and how they continue to develop skills after the workshop ends.  

• Can the provider deliver consistently across regions, languages, and formats (live, virtual, digital)? 
• More importantly, what’s the plan for reinforcement after the initial rollout, so this doesn’t become a one-time event?

In Practice: When Richardson rolled out a sales methodology to 40,000 sellers and managers across IBM's global organization, the real win was the management coaching cadence built to sustain that scale. That cadence contributed to $1B in additional revenue. 

Read the full IBM case study to learn how IBM chose Richardson and how our continued partnership drove global transformation.

How should you score RFP responses?

A good set of questions still needs a scoring system that turns answers into a decision, not just a stack of PDFs. A few principles worth building in before the RFP goes out: 

• Weight the categories before you send the RFP, not after. Decide how much strategic alignment, methodology, AI and technology, coaching, and scale each count toward the total, and lock those weights before responses arrive. This keeps the process neutral and prevents justification of “favorites” later on.
• Separate mandatory gates from scored criteria. Some requirements are pass/fail, such as security standards, minimum industry experience and language coverage. Categories that are not pass-fail should be scored on a 1–5 works well, and it's what the evaluation matrix above uses.
• Use more than one scorer, and have them score independently first. An odd number, three or more, avoids a deadlocked tie. Have each evaluator score against the same rubric on their own before the group compares notes, so early opinions and groupthink don't flatten the discussion before it starts.
• Require a short justification with every score. A number without a reason is hard to defend later, especially if a stakeholder asks why one provider scored higher than another.

What does the evaluation process look like after scoring?

Scoring the written responses narrows the field. It shouldn't be the only step. 

• Shortlist to two or three finalists, then go deeper. A realistic RFP shortlist starts around five vendors; after the written review, narrow to one to three before investing more time.
• Run structured demos, not vendor-led ones. Give every finalist the same script and the same data to work with, so what you're comparing is the solution, not who has the better presenter. Score the demo on the same scale as the RFP itself.
• Check references with real questions, not a formality. Ask what the promised timeline was versus the actual one, what came up that wasn't in the original proposal, and whether the reference would choose the provider again.
• Consider a short proof-of-concept before you sign. For AI-powered practice or coaching tools especially, a two-to-four-week trial using your own scenarios and data tells you more than any demo can.

What mistakes do buyers make when evaluating vendors?

Even a well-built RFP can go sideways in how it's used. Watch for these five mistakes: 

• Treating price or certifications as the primary decision criteria. Both are easy to compare and neither predicts whether sellers actually change how they sell. Weight them last, not first.
• Being impressed by AI features that aren't tied to a specific behavior-change outcome. A slick demo proves the technology works. It doesn't prove it changes what a seller does in a real customer conversation. Ask what behavior it's built to change, specifically.
• Skipping manager/coaching capability in the RFP entirely. Training that never reaches a seller's manager rarely survives past the first quarter. If coaching isn't in the RFP, it won't be in the proposal.
• Not asking how the provider measures behavior change vs. completion rates. Completion tells you who showed up. It says nothing about who sells differently afterward. Make providers show you which one they're actually measuring.
• Waiting until after signing to think about scale, localization, or reinforcement. These aren't implementation details to sort out later. They determine whether the program survives contact with a global, distributed sales org. Put them in the RFP, not the kickoff call.

Frequently Asked Questions about Choosing a Sales Training Provider

Q: What should be included in a sales training RFP? 

A: A sales training RFP should evaluate five things: strategic and buyer alignment, methodology rigor and proof of behavior change, how AI and technology are actually used, coaching and systems integration, and the ability to scale and sustain results. Most RFPs stop at price, certifications, and delivery format, which tests for the wrong things.

Q: Should a sales training RFP ask about AI and technology capabilities?
A: Yes, but ask how AI is used, not whether it's used. Nearly every provider will claim some AI capability. The more useful question is whether that AI orchestrates behavior change across assessment, practice, coaching, and reinforcement, or whether it's a single feature bolted onto an older model. 

Q: How is sales training methodology different from sales training content?
A: Content is what sellers are taught. Methodology is the proven framework that defines which behaviors actually drive outcomes, so that content, coaching, and measurement all point at the same definition of "good." Training built on content alone teaches concepts; training built on methodology teaches behaviors that can be observed, coached, and improved. 

Q: How long should a sales training provider evaluation take?
A: There's no fixed timeline, but organizations should avoid rushing past the two steps that matter most: a real assessment of what your sellers need, and reference conversations with the provider's existing customers.  

Q: How do you measure ROI on a sales training program?
A: By measuring behavior change against defined, observable criteria, then connecting that change to business outcomes (win rate, deal size, cycle time) not by measuring completion rates or satisfaction scores. If a provider can't describe how they'll measure behavior change before training starts, they won't be able to prove ROI after it ends.