B2B: 8 Reasons Why Your Sales Team Might Be Losing Pitches Ask an Expert

By Sean Campbell on November 28th 2017

Are you losing deals because of your sales team’s actions?

After more than a thousand market research interviews in the B2B tech field, we’ve collected some of the most common mistakes that sales reps make.

These insights have been gathered from hundreds of interviews with B2B tech decision-makers, product evaluators, customers, and partners.

Here’s how to recognize and avoid these common sales blunders.

1. Not getting up to speed

No prep, no win.

At least half of the lost deals we investigate are due to sales teams demonstrating a lack of knowledge of the buyer.

B2B customers need to know that the company they’re buying from understands their industry. Sales reps need to show either first-hand experience or extensive book knowledge of the customer’s industry.

Actually, B2B sales reps should be so knowledgeable that they could easily skip the first few days of training if the customer were to hire them tomorrow.

Sales reps should also be able to speak their customers’ industry jargon fluently. Sure, it’s okay to ask what an acronym means but no more than once or twice in a sales meeting. More than that and customers will be seeing red flags.

2. Oblivious to why the customer is looking to buy

Importantly, B2B sales reps need to know what jobs buyers need a solution to solve.

We often see sales reps who can sing the virtues of their product but have no idea what job customers will use it for. Not good.

B2B sales reps need to be able to explain how their product can satisfy customers’ “jobs to be done.”

3. Over-reliance on the pitch deck

Real-world sales conversations don’t fit neatly into a PowerPoint or script. B2B salespeople should be confident enough in their knowledge not to panic if the dialogue deviates from the pitch deck.

Great B2B sales reps are always ready to dive right into the demo. We’ve literally never heard a complaint that a vendor gave a proof-of-concept or demo too early on.

Quite the reverse, actually. We often hear grumbles that sales reps spend way too much time on the slide deck before getting to the good part.

Though some customers may enjoy the PowerPoint view of a product, others consider it as a waste of time. Adjust accordingly.

Always assume that the competition is proving their product’s worth in an attention-grabbing, mind-blowing demo. If that’s the case, how much time do you want your sales team to spend droning on about the product before showing off what it can do?

4. Not knowing the buyer personas

Far too often, we suspect that B2B buyer personas never get shared beyond the marketing team.

Trust us, the rest of the company needs to know those buyer personas too. Especially sales.

So many sales teams go-to-market with one pitch targeted at a single buyer persona.  This automatically eliminates all other potential customers. It’s not wise to have such a limited sales approach.

B2B sales reps need to know whether they’re talking to the CFO or IT admin and tailor their message accordingly. Obviously, these two personas care about different things.

Don’t get into the weeds with an executive but dismiss the IT admin’s questions around configuration by flashing screenshots of dashboard reports at them. Instead, a successful pitch would carefully address both persona’s concerns.

Speak to all the buyer personas in the meeting.

5. Forgetting to talk about ease-of-use

It’s fair to assume that all potential customers care about how easy the product is to use.

Usability concerns are often responsible for lost deals. Two especially common culprits are:

  • Fear that the product is too complex to implement.
  • Worry that user adoption will be low without significant training.

Ease-of-use should receive a lot of attention in your sales team’s pitch decks and demos.

6. Lack of transparency on total-cost-of-ownership

It may be tempting to “estimate” a lower price for your customers than is realistic by neglecting to factor in related costs.

Don’t do it, though. It will destroy any chance of brand loyalty. Omitting related costs from the estimate may win today’s sale, but it will kill tomorrow’s.

B2B sales reps should:

  • Be upfront about professional service fees
  • Give a realistic estimate of the implementation timeline
  • Explain any additional infrastructure customers will have to purchase

Failing to mention these costs may just create a new customer for the competitor.

Be honest and direct to keep the customer coming back.

7. Not sending enough sales reps

Say a customer arranges a half-day demo with an account rep. They ask three of their colleagues to clear their schedules to attend.

Then a single sales rep shows up and is unable to answer anything beyond the most basic questions. From the client’s perspective, this is a huge waste of time.

To sell to important stakeholders such as senior IT managers and business leaders, sales reps need to be capable of thoroughly answering each of their questions.

However, it’s unusual for a single sales rep to have enough knowledge and context to do this well all on their own. That’s why it’s smart to bring a team.

The sales entourage should include:

  • A strong account rep who understands the buyers’ needs and how the product can address them
  • An expert in industry context and jargon
  • A solutions architect who can demonstrate how the product will be used in a real-world environment

8. Being slow to respond

Obviously, being responsive to leads is extremely important.

Unfortunately, sales teams don’t always know about the lead right away. Large companies especially struggle with this problem.

In many cases, it’s far too difficult for potential customers to interact with B2B tech sales teams.

Sure, the website probably has a “contact us” form but potential customers have no way of knowing who is on the receiving end of that form.

Same issue with the phone. There’s no telling who will pick up that general number listed on the website.

With no clear and easy route to a sales rep, potential customers may leave in search of a more accessible vendor.

Further, even if customers make the effort to leave their email or phone number, large companies often take way too long to get back to them.

This state of affairs puts upstarts at an advantage.

Big tech companies may have larger sales forces than startups, but startups sales reps are often way closer to their companies’ contact us forms, emails, and phone numbers.

In our win-loss studies, we’ve found that upstarts typically get back to potential customers within a day. Whereas large companies may take a week or more to respond.

It’s not hard to guess who will win the deal: the company that responds within hours or the company that responds in a week.

How to do better

These B2B sales mistakes may be upsettingly common, but they are also easily avoided.

Market research can help you figure whether one of these common pitfalls is tripping up your sales team and how to adjust to win more deals.

Special thanks to Colleen Clancy and Isabel Gautschi for contributing to this piece.


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Sean Campbell

Sean Campbell is the CEO of Cascade Insights, a B2B focused research firm with a clear focus on the technology sector. For Cascade Insights, Sean oversees the health of the firm, maintains relationships with key accounts, and leads the company's thought leadership efforts.