Happy Paths: How to design the ideal B2B buying process

Your sales team is trained. The deck is tight. You’ve nailed the demo and ICP. 

But deals are still stalling. Champions go dark. Stakeholders say, "Not now."

The problem isn’t your sales process. It’s the buying process.

Today’s B2B buyer journey is a mess. Decision-makers are stuck in a maze of internal politics, budget scrutiny, and procurement red tape. 

They’re not empowered to buy. They’re forced to prove ROI justification, get alignment, and de-risk everything they do. And they’re doing all of this without a clear playbook or support.

This guide unpacks the modern buying process—what B2B buyers are really up against and how sales leaders can train their reps to shift from pitching features to partnering on the purchase.

Buyer 3.0: The power shift in B2B buying

Wynne Brown, a longtime revenue and success leader at companies like GitHub, RocketReach, and Fable, breaks down the last two decades of B2B sales into three key eras.

Buyer 1.0: Vendor-led

In the early days of B2B sales, sellers ran the show. You could show up, run a demo, and buyers would just try to keep up.

There were few expectations, no internal buying process, and very little pushback.

Buyer 2.0: Information-rich

With the rise of peer reviews and LinkedIn, buyers started showing up more informed. Sales became more consultative. You had to work with the buyer, not just talk at them.

Buyer 3.0: Buyer-focused

Today’s buyers are self-educating, time-starved, and over-informed. They rely heavily on digital channels, white papers, social media, and peer validation before ever speaking to sales representatives.

Because they’re doing all of this on top of their actual job, they take shortcuts. You’ve seen this play out in real life, and data from 6sense’s B2B Experience Report backs it up:

• 4 out of 5 buyers initiate contact once they’re already 70% through their buying journey
• Over 90% of buyers have prior experience with at least one of the vendors considered
• 81% of buyers indicated they have a preferred vendor at the time of first contact
• 85% already established purchase requirements before reaching out

These buying decisions are based on what worked before, not what’s best now. 

And that’s risky business. Gartner shows that purchase regret is 23% higher when buyers avoid speaking to a salesperson.

“All of our buyers are self-educating before they talk to us. So, whether we like that or not, they are going to go out and do a lot of research.” - Catie Ivey, CRO at Walnut

That’s why the best B2B sales reps today don’t persuade. They co-pilot the buying journey. They coach the buying team through the decision-making process and help them avoid purchase regret.

Buying software is a job most champions aren’t trained for

Today’s B2B buyers aren’t just evaluating product functionality or comparing potential suppliers.

They’re leading a complex purchase process while juggling their day jobs. Acting as the project manager, the budget owner, the internal salesperson, and the risk mitigator.

Although the average B2B purchase decision process involves 6-10 stakeholders, the buyer champion does most of the heavy lifting alone. They have to:

1. Define the problem and align on key factors
2. Research B2B vendors and build requirements for supplier selection
3. Attend demos and then put together FAQs, case studies, and testimonials
4. Build internal buy-in with stakeholders across departments and get budget approval
5. Navigate procurement and security reviews
6. Drive onboarding and post-purchase evaluation

The term “buying committee” sounds great on a slide. But companies don’t form formal task forces dedicated to evaluating vendors. Instead, champions chase stakeholders with other priorities and different incentives.

The reality is:

• Champions don’t just build consensus, they spend more time handling objections
• Demo recordings are passed around without much context or conviction
• Pricing is usually forwarded without an air-tight business case

So when it’s time to make a decision, these other stakeholders start asking:

• “What’s the ROI?”
• “How fast can we implement this?”
• “Will I have to be involved?”

If our champion doesn’t have the answers, the deal stalls. Or worse, it dies.

It’s not a buying group. It’s a one-person army.

The top 4 reasons why deals stall (and what to do about them)

You can’t sell your way past misalignment. The real roadblocks are inside the buyer’s organization.

1. Wrong stakeholder, wrong expectations

Many B2B sales reps get stuck selling to someone with influence but no authority.

As Pete Prowitt, Head of Revenue at Stytch, puts it, “Sometimes we assume our champion is a decision-maker, but they’re really just a coach. You have to test early: Can they actually drive the deal forward?”

How to fix it

Use account mapping to identify gaps, visualize stakeholders, and identify blockers early.

Stephen Ruff, Co-Founder of Champify and former AE at Heap, avoids making a hard ask for another leader’s time. Instead, his team co-creates a Dock workspace with the champion as a conversation starter.

“If we realize we’re not talking to the right person and need to thread out to a leader in an adjacent department, Dock gives us a great way to do that.”

Because Dock tracks who views the shared workspace and what they interact with, it naturally surfaces other decision-makers who should be involved in the deal. You can see exactly who’s engaged and where you might need to follow up without having to bug your champion.

2. No clear business case

Your champion needs ammo to fight for budget. Without a compelling ROI narrative, the deal dies in procurement or CFO purgatory.

How to fix it

Ingrid Murra, CEO of Two Front, realized she had to make the business case crystal clear for her customers.

“Our biggest challenge was convincing them they’d make more with us,” she said.

She now creates Dock workspaces that include revenue model comparisons, pricing structures, and testimonials. Since making the shift, she’s generating 30% month-over-month growth.

3. Late-stage surprises

Bringing in legal, IT, or security too late is a surefire way to block or blow up a deal.

Noah Massucci, Director of Sales Engineering and Customer Onboarding at Robin, knows this all too well. His presale team gets tapped in during the sales process to help customers with their evaluation and address technical or security concerns before the deal closes.

“A typical challenge for our Presales team is they're getting involved after conversations have happened,” said Noah. “They're trying to catch up and understand: Who is this person I'm talking to? What are their goals?”

How to fix it

Noah’s team now joins the sales cycle earlier, looping in tech stakeholders and sharing onboarding plans, security certifications, and requirements upfront. They can easily pass on timely and accurate information between teams as deals progress.

“It levels up that conversation so that we can not only just talk about the product functionality but also the impact of implementing and integrating Robin with your current systems.”

This makes life easier for technical buyers, who now have one place to go for information.

“We're already starting to implement things like security review access, where you create the security page template [in Dock], and allow people to get access to an NDA, our pen tests, our certifications, all of that.”

As a result, not only has the sales experience improved, but Robin has been able to cut implementation timelines by 30 days to just one month while maintaining high customer satisfaction scores.

4. No visibility into the decision-making process

Most B2B buying decisions happen in meetings you’re not invited to.

The worst part is that reps don’t know who is attending those meetings or when they’re happening. We’re at the mercy of our champion.

How to fix it

Use engagement analytics to track buyer activity. Time your follow-ups around internal meetings, not sales stages.

Through Dock’s notifications, reps can get a follow-up signal before a buyer’s internal meetings. Andrew Hollis, Co-Founder and Director of Sales at Nectar, leveraged these to increase win rates by 31%.

“If it's a few weeks before we're having our next follow-up and they're searching around in the Dock, it's a safe assumption that they're either having a conversation with somebody or they're prepping to do some type of presentation.”

“So we use that as a touch point and own up to it. ‘Hey, I saw you were clicking around on the Dock. Any questions I can answer?’”

By jumping in at the right moment, they can help their buyers champion Nectar’s cause.

Train reps to train buyers

Sales reps are already multitaskers. But the modern sales process demands a new skill set rooted in buyer enablement.

Good news: these skills are tough to replace with AI. 

Bad news: we’ll have to train sales teams differently. 

To enable modern buyers, reps need to take on three new responsibilities.

Software evaluation guide

Ninety-four percent of IT decision-makers want help evaluating products from vendors. 

That includes refining product specifications, validating solutions, comparing RFP responses, shaping criteria, and defining success metrics.

This is where most reps miss out on a huge opportunity.

It’s not about having all the answers. It’s about becoming a thought partner in the process. 

Great reps do this by asking thought-provoking questions, helping buyers clarify what they’re solving for, and sharing insights from past evaluations. Instead of pushing features, they help the buyer weigh trade-offs, challenge assumptions, and align stakeholders around a shared definition of success.

“You get to teach them how to buy software. They’re not numb to marketing — they actually respond to being educated.” - Joseph Schmitt, SVP Customer Success at UpKeep

Still, we often blow past this part. We decide the buyer has already done their homework, or just doesn’t want to hear from us. 

Reps who support this process early influence the purchase decision. The ones that don’t end up wasting time filling out forms.

As Matt Green, CRO at SalesAssembly, puts it: “If you're not part of the planning committee, you're part of the entertainment.”

So how do you get on the planning committee? By not waiting to be asked. 

We need to earn our seat by sharing common “watch outs” from other evaluations, suggesting criteria buyers often forget to include, and offering examples of how similar teams ran their process from shortlist to sign-off. 

When you bring that kind of experience to the table, you're not just helping them evaluate your product. You’re helping them run a smarter evaluation overall, which makes you indispensable.

Implementation consultant

Implementation starts during evaluation. It’s an opportunity to show up smart by:

1. Framing mutual outcomes, risks, and responsibilities before the deal closes
2. Sharing a battle-tested plan to get rid of fear, uncertainty, and doubt
3. Tying it all back to the overall strategy and reminding prospects why they chose you

One way to do this well is by connecting the implementation plan to their bigger-picture goals.

“We feed the company’s 10-K into ChatGPT and identify what matters to their R&D team,” says Jellyfish’s VP of Sales, Ben Solari, “That’s how we link to their strategy.”

This kind of proactive planning matters more than ever, because buyers are overwhelmed. 48% of B2B companies need six or more approvals to complete a new product purchase, and they’re evaluating 50 new vendors a month.

To stand out, reps need to bring more than a pitch. They need to walk in with a plan that proves they’ve done this before.

Dock’s mutual action plans (MAPs) help you co-design that plan with stakeholders, turning implementation from a question mark into a clear path to value. Tasks are assigned, deadlines are tracked, and everything from pricing decks to onboarding docs is embedded in one place. 

Even if a new stakeholder joins late, they can quickly get up to speed on what’s been discussed, where the deal stands, and what’s left to move forward. 

That level of clarity matters because 78% of B2B customers expect ROI within six months of purchase. If you can’t help them see how they’ll get there, you risk shelfware. Low adoption = zero chance at renewal.

Change management partner

Your buyer isn’t just choosing a new product. They’re driving organizational change. And they need a clear way to bring stakeholders with them.

To help them succeed, reps need to think like change management consultants. That means giving your champion a single source of truth they can use to build partnerships with IT, finance, legal, and leadership teams.

Robin’s sales and customer success teams use Dock to do just that. Instead of scattered email threads and siloed handoffs, they create one consistent experience from first call to implementation.

As Noah Massucci, Director of Sales Engineering at Robin, put it:

“We wanted the customer to feel like everyone was connected and communicating.”

His team now uses Dock to keep stakeholders aligned on goals, timelines, and tasks before and after the deal closes.

This is how reps can become trusted change agents, rather than just vendors, by directly improving the customer experience through every step of the B2B customer journey. Not just the sale.

Track the buying process between deal stages

Deals don’t die in demos. They die in the gaps of the B2B purchase process.

The most painful delays happen between stages—after discovery but before proposal, or after the demo but before procurement. It’s where champions lose steam, stakeholders lose track, and momentum disappears.

This is where deal visibility matters most.

Dock gives you real-time insight into stakeholder engagement across touchpoints. Because all sales materials live in a shared Dock workspace, you can see exactly who’s interacting with what in meetings, between stages, and behind the scenes. 

When a new stakeholder opens the pricing proposal, or the champion revisits the onboarding plan before procurement, you get real-time visibility into deal movement that would otherwise go unnoticed.

Sales leaders and customer success teams can see what content is being viewed, who’s getting involved, and when key decision-makers are preparing for internal meetings.

You only get so many chances to move a deal forward. Dock helps your sales team show up at the right moment—with the right message—to keep buying decisions on track.

As Helen Ralowicz-Chapman from Marqii sums it up:

“It’s really helpful to go back and have those archives of what the initial problems and pain points were, and what we can do for them now.”

That historical context isn’t just helpful for follow-up. 

It keeps momentum going, prevents misalignment, and helps sales and customer success stay connected to the “why” behind the purchase even months later.

What’s next: the future of B2B buying

Look, I’m not going to pretend to have a crystal ball. No one knows exactly what the B2B buying process will look like in five years. But the trend lines are clear.

AI-first evaluation

Business buyers are already using AI to build shortlists, write RFPs, and assess potential suppliers. Sales messaging needs to cut through that noise with high-quality insights and problem-first positioning.

It goes back to the idea of Sense Making and Buyer 3.0. Today, buyers are flooded with too much information. They’ll still want a human in the loop to guide them through the final steps of evaluation. 

Experience and expertise will matter even more, and prospects will be willing to pay a premium for it. The rep who knows the space the best and can earn trust fastest wins.

Self-serve with scaffolding

We already know that buyers want to explore tools independently before talking to reps. Self-service and product-led strategies are table stakes. 

But being “product-led” doesn’t mean being completely hands-off.

Buyers still need support, especially when it comes to navigating pricing, internal approvals, or evaluating enterprise readiness. That’s where a combination of sales assist and digital sales rooms shines.

With Dock, you can “scaffold” the self-serve journey by pairing interactive demos and docs with contextual nudges, real-time chat, and personalized video walkthroughs inside a shared workspace. It gives buyers the freedom to explore while still feeling confident that help is a click away.

This kind of enablement pushes deals forward. It ensures that B2B decision-makers and end-users both have everything they need to buy—without waiting on a rep, but without feeling like they’re on their own.

Personalized follow-up

Follow-up is still one of the biggest problems in sales. According to Helen Ralowicz-Chapman, “It takes eight connection attempts to get attention, but 44% of reps give up after one.”

That’s what Dock AI was designed to solve.  Dock auto-generates follow-ups, business cases, and personalized workspaces from sales calls–so your reps can deliver a completely tailored experience.

Not only does this improve the speed and quality of follow-up, but it allows reps to focus on other value-add activities. They can dedicate more time to research, strategic touchpoints, and multithreading.

Sell the program before the product

In B2B sales, the final decision often hinges on trust.

That’s why the best sales reps are strategic advisors. They help B2B decision-makers frame pain points, clarify goals, and build a case for change that resonates across the buying group. 

That means building a program around the product, not just jumping into feature sets. It means anticipating stakeholder pushback before it happens.

Dock helps make that possible by helping you put everything your champion needs to win the sale in one place. Want to make it easier for your buyer to say “yes”? 

Try Dock for free. The first 50 workspaces are free.