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Founder Insight

The B2B Sales Best Practices Playbook

How to build a healthy sales pipeline, close deals faster, and set up a sales pipeline for hypergrowth

Shilling Team
15 July 2022

Beyond “Build it, and they will come”

So, you’ve created a great product. You’ve done your research and believe you have a good market fit, you’ve found people who believe in your company as much as you do — co-founders and investors, and now you’re out to get customers by highlighting how awesome your product is. After all, “build it and they will come” right?

Not so fast.

The bad and good news is: B2B sales is not really about your product. 

It’s about the problem it solves, and the people who need it fixed. 

Selling to a B2B audience is all about building trust and getting to know the buyer. As a start-up founder or salesperson, you’re also facing the additional challenge of selling to more established companies when you don’t have brand recognition. Like Sofia Pessanha said in the “Rise to the top” podcast when discussing her path as a founder and investor, “Why should customers give you their money, give you their time, give you their energy?” 

That’s where we come in.  As an early-stage VC, we at Shilling have been helping startups figure out their path to growth for over ten years. We’ve also gathered insights from the B2B sales workshop we led in Lisbon, where we heard from sales experts and 20 portfolio founders about their biggest sales challenges, and shared tips on how to tackle them.

This practical guide to B2B sales collects all that knowledge sharing, collected for founders and sales teams in early-stage startups that are building up sales processes from the start.

Know the customer

During our workshop it quickly became clear that one of the biggest issues for B2B start-up founders is getting leads interested in a first meeting, and then moving them down the funnel. 

How do you convince them your product is worth 20 minutes of your time?

B2B sales tend to be much more complex than B2C. They involve more money and commitment, and as all humans, buyers are naturally adverse to change and risk. Especially when they need to justify it to their boss.

The sales cycle (from Lead to Close) averages 102 days according to industry benchmarks, but if you’re trying to sell to enterprise companies it may be closer to a year, and that’s a lifetime in start-up years. To make this process more efficient, you need to start by getting to know your customer, their needs, and who needs to be involved. 

No amount of googling will tell you all the answers (although some research is advised). The only way to find this information is to simply ask the right questions.

Create buyer personas

Asking open ended questions and being curious during the exploratory phase will help you understand how buyers see your product, what are their priorities and key features, and who else should be involved. The next step is to make sure you turn this information into a process that can scale as your team grows.

That’s where buyer personas come in.

A buyer persona is a profile of your ideal customer that will help drive your overall company strategy, from product development, to marketing, to lead generation and sales. 

Some companies make their buyer personas very detailed, but we recommend keeping it simple and focus on 3 key profiles of the decision makers you need to win.

For SaaS businesses can include among others:

  • Final user: the individual or manager of the team who will actually use your product on a day-to-day basis
  • Finances: the one who will ultimately write the check. In small to midsize companies it can be the CFO, but in enterprise sales it can be a procurement manager
  • Tech/security: the people who will do final checks on compliance and implementation

Once you define who are the key personas in your sales process, use the information you’ve gathered and fill out a basic profile:

Other buyer information goldmines you should explore to build a buyer persona:

  • Customer interviews
  • Ask your current customers why they picked you, what are the features they’re missing, and how they use and describe your product.

  • Customer support
  • One of our portfolio companies made it part of their culture that everyone, from the CTO to the SDRs, had to answer customer support tickets. This helped the whole team be aligned on what customer’s pain points and priorities. 

  • Lost opportunities
  • Nothing worse than being rejected. But whether through email or a quick call, if a deal falls through try to understand the why, if they ended up going with a competitor, or not buying a product in your category at all.

Invest in more than one stakeholder

As we covered, B2B sales may involve a whole committee of decision makers, many of which are not your product’s final users. This is why, according to Gong research, B2B win rates are 2 to 3 times higher when you build a relationship with multiple people within an account.

That’s why it’s so important to “go broad” when it comes to deal execution and spend the time  building relationships with multiple people within an account. 

Whether you target these people with outbound efforts, or get lucky and find new champions cc’d in one of your emails, you should aim to get them involved early in the funnel. After all, as we shared in our workshop, “in B2B sales, you don’t lose the sale on the meetings you have, it’s on the meetings you don’t.”

Key takeaways

Why you should aim for the group call:

  • Go from selling a solution to an individual to selling it to the business
  • Get over objections quickly
  • It’s a clear buying signal: use it to guide your forecast

What to watch out for:

  • Everyone gets real quiet when the boss attends, change how you ask for feedback
  • Avoid getting tangled in internal miscommunication or misalignment
  • Keep on message and a tight agenda, don’t get derailed

Tailor the value proposition and message

On our “Race to the top” podcast episode with Sofia Pessanha, LP investor and co-founder of CareRev, spoke about the importance of iterating your value proposition as you get to know your customer.

“Now we describe CareRev as a workforce management tool for hospitals. That is not what we said when we started the company.”

Words matter. When you speak the same jargon and terms as your buyer you’re building trust that you know what you’re doing, you know the industry and you understand their pain points.

It’s also key that you adapt the value proposition, and your message, to the buyer personas. 

For example, CareRev’s value proposition for nurses was always clear: this app will help you manage shifts and get paid easier. As one of the co-founders is a nurse, and the product had been built with them in mind, “the message was crisp from day one.”

The message for hospitals, the buyers on the B2B side, was murkier. It took listening in to a lot of sales calls, and really diving deep into the healthcare industry, to segment and adjust the message to different realities.

Key takeaways

  • Buyer persona
  • How will they use your product? What do they value most about it?
  • Target account size
  • Is it a smaller company or an enterprise? How will your message differ?
  • Keep listening and testing
  • Ask questions, listen in to sales and support calls, and iterate on your message
  • Don’t talk like a salesperson
  • Build trust, respect, and empathy by using the same language as your buyer

Understanding the sales funnel

Stop us if you’ve seen this one before: 

There’s a reason why the acquisition funnel is so widely used: it’s the easiest way to visualize your customer journey. 

But do you know what signals to you that buys are in the awareness stage? What’s their entry point into discovering their product? What about intent, what actions indicate that?

Failure to answer those questions means wasting time going after the wrong leads, being overly optimistic in your forecast, and risking misalignment that may cost you opportunities both with buyers and investors.

A sales funnel is only useful if every step is practical and measurable

Usually, marketing teams are the ones responsible for handling inbound lead generation (and moving down their own funnel), but since many early-stage startups don’t yet have that structure — you the founder may even been doing it all by yourself, we’ve also included tips to fill the top of your funnel with lead generation.

  1. Awareness

Despite common misconception, the “awareness” stage is not about buyers being aware of you or your product. 

Instead, it’s about their pain points and trigger, awareness stage leads should be frustrated enough by their issue to be actively looking for solutions.

Turn it into lead generation

  • SEO
  • Produce helpful content focused on pain points, not focused on your product or brand
  • Social media
  • Watch for disgruntled leads talking about your product category on LinkedIn and Twitter using keyword search
  • Start the conversation by interacting and being helpful
  • Events and webinars
  • Partner with well-known brands and attend industry events 
  • Word-of mouth
  • Happy customers are your best (and cheapest) lead gen channel
  • Implement a referral program for customers

  1. Discovery

Buyers in the discovery stage are aware they have an issue and actively searching for solutions. 

Focus on getting eyes on your product and highlighting key benefits like implementation, ease-of-use, and price.

Nurture discovery stage leads

  • Newsletters and gated content
  • Nothing’s more precious than someone’s email, so if a lead signs-up for anything it’s a great sign of interest
  • Follow-up with a personalized message
  • Reach out directly to ask them if they have any questions and offering your help
  • Set up a call to ask them about their issues and pain points
  • Maintain the relationship
  • Follow them on socials, offer a free trial, and make sure you track clicked links in emails and landing pages

  1. Intent

Intent is often the easiest one to define and measure: the buyers have decided to buy a product to help solve their issue and you’re in the running.

Clear intent indicators

  • Requested a demo or free trial
  • Other stakeholders are involved
  • Discussions about implementation, timeline and pricing
  • Follow-up calls on a clear timeline

  1. Evaluation

Time to see how you stack up against competitors. Don’t be afraid to ask if buyers are evaluating other solutions and if there’s any key feature they feel you’re missing. 

Make sure buyers expectations are aligned with what your product can deliver.

By now, you should also know the buyer’s decision criteria and who will have final say. Otherwise, you risk being stuck in evaluation limbo.

Key decision factors

  • Numbers and ROI? 
  • Clearly showcase benefits like time-saved and personalized customer support, and consider offering a discount or negotiating payments
  • Referrals and reputation?
  • Set up a call with an existing customer who loves your product to ease their mind
  • Implementation and ease-of-use?
  • Have your tech team join the meetings and offer training materials
  • Introduce them to the customer success manager who will be in charge of the account
  1. Buy

It’s a win! Or is it? Be on the lookout for legal issues, last-minute-questions, and any implementation concerns. 

Then, move the account along to the customer success stage, where you can restart the process in a few months to upsell and grow their contract, or turn them into a champion.

Future-proof the sales process

A frequent challenge for startups is to keep track of all the information you’ve gathered as team’s restructure and grow. When you’re the founder who’s also making sales calls it’s easy to know exactly your message, ideal customer profile, and how much of a discount you can offer, but all that needs to be out of your brain and understood by your team.

Encourage your team to follow and learn from sales gurus like Kevin DorseyJosh Braun, and Armand Farrokh, and make sure you create space for them to experiment and share learnings. You want to write down what works and what doesn’t, not only to make your current team better, but also to set-up for the future. 

Create alignment

Price, the elephant in the room

So let’s rewind a second and talk about pricing and discounts. Many of the founders at our workshop had a lot of questions surrounding it, as price tends to be a huge deal breaker in most deals.

  • When should you bring it up?
  • Should you avoid telling an early-stage lead the price?
  • Will it scare them off?
  • Will it ruin the sale?

There’s basically two schools of thought:

The first is that you should share price as early as possible in the discovery process, basically as soon as it comes up, even if it’s through email. Our friends at Gong have put together some pretty strong data that indicates win rates are highest when price is discussed right on the first call, up to 42% higher.

The reasons why it’s good to get it out of the way early are pretty clear:

  • It builds trust and a sense of transparency
  • If price will be an issue, sharing it early is more respectful of yours and the buyers time

The second common approach you’ll see seasoned B2B sales veterans take is to make price one of the last things you mention.

The theory here is that price can become a blocker before you even get to make a case for your product or present your value proposition. By talking about features and benefits first, hopefully price will no longer be the center of attention and when it does come up, your customer will understand why things cost what they do.

There’s also some data to suggest that which one is better may be related to culture. Southern Europeans, for example, tend to prefer price to be discussed later, as they find it awkward to do it right away, but in countries further north it can be seen as sleazy and untrustworthy to not be open about the price.

A good compromise, according to Gong’s research, is to bring it up early in the funnel, but later in the call, finding that top performers tend to bring up price at the 38-46 minute window of the first call.

One thing you do need to be aware of is that the minute price is brought up, you’ve now entered negotiations.


For startups desperate to build brand reputation and full of sales teams hungry for wins, discounts are pretty much a part of the game.

Unfortunately, they also become challenging pretty quickly, especially if they become an escape for your team, and the only way they can close sales. Eventually, discounts start cutting into your bottom line, and they also become expected from future clients. It’s unlikely a customer you’ve closed on a discount will ever pay full price, so they should be managed extremely carefully. 

If your sales team is always falling back on discounts, it’s time to step in by helping them grow professionally. Consider additional training, shadowing calls, and working on ways to effectively communicate your value propositions and handle common objections.

Also, set up clear rules, such as:

  • Only offer discounts in odd numbers (e.g 23%, 19%, 34%)
  • Blame it on human psychology, but odd-number prices and discounts make buyers less likely to try and negotiate further
  • An even number discount (30% or 25%) seems more open ended to growing in 5% increments, so keep it ood
  • Be clear with your sales team on what’s the max discount ceiling
  • Put down a limit to how many discounts sales reps can use per quarter

Encourage them to think about other negotiation tools

  • Play with payment and contract terms
  • Highlight the quality of your customer support versus competitors
  • Offer early-access to new features

Challenge Outbound: When does your team mention discounts?

One of the things you will want to pay close attention to with your team is not just how often they are resorting to discounts, but also at what stage in negotiations? Ideally, you want it to be as late as possible.

What sales-enabling tools do you need on your tech stack?

Especially with a small team, don’t fall into the trap of trying to find the “perfect sales tool”. It  may be more urgent to invest in a CRM like Hubspot, that will help you collect emails and inbound leads, and feed them to your sales team. 

For lead discovery and qualification, LinkedIn Sales Navigator also works great, but so does investing a lot of research into leads, and then organizing them in Google Sheets. 

If the thought of even more spreadsheets just made you break out in a sweat, a tool like Rows can help. Rows integrates your spreadsheets with other apps you’re already using to help sales and marketing teams track and enrich data.

It all depends on your team's needs and budget. 

With that in mind, our advice is to find the easiest tool that helps your sales team respond quickly to new leads, and promotes alignment. 

Metrics you should track

You know the deal: you can’t improve what you’re not measuring. Here are some of the main metrics to keep track even if you’re still to raise your first round:

In conclusion, “why should I buy from you?”

“Why should I buy from you?” when heard late down the sales cycle should make alarm bells go off. During the workshop, we jokingly said “never answer it, it’s a trap!” 

We did end up giving practical tips on how to answer this question: turn it around on the buyer asking about their pain problem and how they plan on solving it, remind them how important this is to them as well, discuss product features and messaging, etc.

It works because what buyers are looking for when they ask “Why should I buy from you?” is reassurance.

In one of our B2B portfolio companies, Unbabel, their VP of Marketing was known for saying “businesses don’t sell to businesses, people talk to people.” And we know that people don’t like change, we’re risk averse and fond of being comfortable in our own bubble. 

So, really, despite all the tips and learnings we’ve shared above, the number one tool to succeed in B2B sales is to remember the person on the other side, show them empathy and listen to their problems. Then, do what you wanted when you first came up with the idea for your company: help them solve them.

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