5 Mind, Process & Productivity Hacks For Startup Sales – Lessons From Groupon’s Early Days

On the most basic level, there are only two jobs that a startup founder has: Ship the product. Sell the product. Both are tough, but I know from personal experience — and from conversations with many other startup founders — that sales is often the most challenging of the two, especially if you are bootstrapping. Selling a paid product? There is no product-market fit until you have a customer who’s willing to part with their dollars.

When it comes to the SMB market, the sales challenge can be tricky. Small business owners don’t often have big budgets or lots of time at their disposal. So how can you build a scalable process for reaching them one-by-one, convincing them to listen to your pitch and earning the their business? You can start by learning about how one famous startup did it: Groupon.

I tracked down Sunjay Agtey, one of Groupon’s first salespeople, to pick his brain. He joined the company the year after it launched, when there were just 30 people on its sales team and when the entire company had fewer than 100 people, total. (For comparison: today’s Groupon’s headcount totals over 10,000 employees.) Sunjay was excellent and generous enough to share with me his inside perspective on how Groupon built a sales machine from the ground-up. And here are the most valuable lessons that any startup founder can apply to build an SMB sales juggernaut.

1. You’ll have to do everything yourself at first, but don’t panic.
Today Groupon has a massive sales organization with highly specialized roles, including business development reps, account executives, inside salespeople, outside salespeople and more. But in its early days it was a much flatter sales organization, says founder and former chief executive, Andrew Mason:

“[W]e started off with a team of about seven people. We had a couple of business development guys as well as the guy that was actually doing the writing. Even I was doing it to some extent early on. We were all calling the businesses.” [Emphasis added.]

Sunjay confirms. There was no separate team to hunt prospects and decide whether they qualified as actual leads before passing them on to the person who would do the product demo, follow up via multiple contacts and close the sale. If you were a salesperson in Groupon back in 2009, you were responsible for the entire process end-to-end — finding the prospect, deciding if they qualified as a lead, entering their data into the CRM system, contacting them, doing the product demo, following up and closing the deal. So if you are at the helm of a small team of founders — or even if you are the solo founder — know that it is not at all uncommon for you to also be the chief salesperson. Take courage from the fact that it can be done.

2. Don’t buy lists, build them with your own creativity.
Before you can start reaching out to prospective customers you need to locate them and uncover their contact information. How did Groupon do it?

Believe it or not, the internet was where Groupon went hunting to fill its pipeline of prospects. If you are looking for local businesses, websites like Yelp, Thrillist, TripAdvisor and local blogs are all places where you can find them. But only make those your starting points, and not your stopping points. Go several steps further to uncover websites, directories and other free sources that are off the beaten track — remember that the more creative you can be in finding your lists of prospects, the less likely you are to run into competitors who are using the same hunting grounds.

3. (Dis-)qualifying your leads is crucial.
Sales is a game of numbers. The key to doing it well is finding ways to boost the chance that the very time-consuming activities you are undertaking — calling, emailing and following up on a one-to-one basis — will actually result in a sale. A major part of this is qualifying your leads, or making sure that the small business you are about to contact is actually someone who would be an ideal fit for your business.

The sooner you can determine whether a lead is qualified, the faster you can close a sale: either with that same person or by moving on to someone else in your pipeline who is qualified. To turn the process on its head, you may want to aim to disqualify leads as quickly as possible. Why?

Having the door closed in your face can make sales a bruising sport, but the reality is that you are far more likely to hear “No” instead of “Yes”. For this reason, salespeople can fall into a trap of seeking the comfort of having a fat pipeline of theoretical “Maybes”. But if you haven’t carefully defined what makes a good customer for your business vs. a bad customer — and forced yourself to apply this standard with rigor — you will end up wasting a lot of precious time.

Remember that it’s not the quantity of the leads that count, but rather the quality. If it’s going to be a “No” due to a bad fit, then you’ll want to find this out as soon as possible to avoid wasting time on both sides. In Groupon’s early days the company only wanted to work with small businesses who had a website. So any business that didn’t have a website was a poor lead that would be disqualified. (Or, back in the very early days the Groupon salesperson might occasionally offer to create the website for them. Really. Remember point 1? Expect to do everything yourself.)

4. Learn to live by the clock.  
Efficiency always matters in a startup, but it matters especially if you are a sales team of one. Very simply, the way you approach and structure your workday is going to determine whether you’re able to hit your sales goals. And that, in turn, should be driven by the workday of the people you are trying to reach. Working at Groupon during its early days, Sunjay and his fellow salespeople learned early on to start with the customer and work backwards in order to develop some rules of thumb for the best and worst times to call a small business in a particular industry. Restaurant owners, for example, were usually unreachable between 11am and 1pm, during the lunch hour rush. Instead the team would reach out between 7am and 9am, when the owner was taking deliveries, catching up on finances or other admin tasks. Another good window was 3pm-5pm, before the dinner prep and rush.

Because small business owners are so time-constrained, if you do manage to speak to them during your initial call, be prepared to give them all the info they need to make a decision, including a demo of your product or service. (This is an argument for having a mobile version of your demo that works — if the person you reach is not in front of their computer, you can have them put the call on speaker and open up your demo their mobile browser.)

If they’re not yet ready to make a decision or don’t have time to fully hear you out, be sure to set up a specific time to call them back. And do take the extra step of confirming that next appointment with them before the day approaches. Small business owners often find their schedules overwhelmed by last-minute issues, which may lead them to stand you up. Be intentional about the language you use while making that confirmation so that you hold them accountable to showing up for the new appointment. Try to highlight the benefits they stand to miss out on if they miss speaking with you — a tactic that takes advantage of our cognitive bias against loss avoidance, aka FOMO.

Finding prospects, entering their details in the CRM system, following up on earlier contacts and then entering those results in the CRM — sales during Groupon’s early days was an admin-heavy task. When can you find time to get this done, amidst the actually calling and emailing? Sunjay and his most successful colleagues learned to get these type of tasks done during the in-between periods, i.e. the times that were less favorable for reaching out to the businesses.

Even with a founder’s level of passion, sales can be a repetitive and ego-damaging activity. So be sure to structure your working day in such a way that it’s as palatable as possible for yourself. Maybe it’s doing a batch of calls and then taking a walk around the block before coming back to do email follow-ups and CRM admin. Or taking a few hours at night to set up all of the following day’s emails in your outbox. Find a rhythm that works for you so that you can keep going with peak energy and motivation.

5. Keeping a cool head will help you persevere.
Here’s a bit of folk wisdom: “Sales is a lot like being a parent, showing your baby to the world and having them tell you it’s ugly.” Your feelings may get hurt, again and again. But this will be particularly tough if you don’t accept this as an inescapable part of the process and find a way to develop some amount of emotional distance and move on.

The philosophy they cultivated during the early days at Groupon? Try not to get too high when you close a great deal and also not to get too disappointed when people say no. Keep an even keel. If you have ten people in a room, on average, two people will always say yes to what you offer, and two people will say no. A good salesperson wants to find those nos as quickly as possible so that they can focus on converting the other six people. And when it comes to the four who are indifferent — bear in mind that they may say no at the start. But no’s just the start of the conversation. Try to understand the reasons behind it and be armed with well-thought out ways to counter their objections. And always expect to receive 13 “Nos” before you give up.

As humans we have a deep need for stories, myths and heroic lore that focus on the glory and conveniently leave out all the messy bits in between. But no matter how big they are today, every startup who reached unicorn or household-name status built its success just one sale at a time. And so can yours.