Wiley Cerilli started his sales career peddling coupons door-to-door. Unsurprisingly, he describes it as “pretty much the worst job ever.” “People would generally hate you no matter what you said,” he remembers. But he did take one valuable lesson from the experience: If you knock on enough doors, eventually someone will say yes.

“People don’t ask for things because they never want to be told no,” he says. “But sometimes being told no is the best thing that can happen to you. It means you took a chance. It can help you get to where you’re supposed to be.”

This was definitely the case for Cerilli, who graduated from his early sales experiences to become VP of Partner Sales and Services at Seamless, and co-founder and CEO of SinglePlatform— acquired by Constant Contact two years ago for $100 million. (You can read his advice for startup CEOs here.)

After building massive sales teams from scratch, he's developed an arsenal of lessons for startup founders looking to do the same thing. In this exclusive First Round Review interview, he shares the 39 pieces of sales advice that have moved the needle for him and his companies the most.

Do the Groundwork

1. You need a scripted sales pitch designed to hit your metrics.In the early days of your startup, all you should be doing is developing the right tactics to sell your products, and this is no easy feat. “It takes months and months of testing to come up with the right formula,” Cerilli says. “At SinglePlatform, we were out selling the product for four months before we even built the beta just to see what was resonating.”

2. Start by selling in person.You want to see people’s unfiltered reactions to your presentation and your deck so you can adjust accordingly. Only after months of Cerilli going out to pitch customers in person did he decide to move sales in-house and work on fine-tuning the script for phone sales.

3. Test many different pricing models. Deciphering the optimal pricing for your product is a cornerstone of your sales strategy. And if you don’t test, you won’t know where you stand. “Only through testing did we discover that we were able to sell more as we increased the price,” he says. “We went from a freemium model to now charging $79 a month for the product, and the rate of sales productivity only went up as we charged more.”

People value your product based on the price tag.

“If you offer anything for free, people will generally be skeptical,” Cerilli says. “They will believe your product has whatever amount of value you tell them. If you charge $20, people will think, ‘Oh, it’s only worth that? I don’t want to spend time on something that’s only giving me $20 worth of value…'"

4. If you undervalue your product, people will use it less. Psychologically, if people haven’t paid for something, they have no reason to use it. “Think about it. If you buy something expensive, like a gym membership, you’re going to use it because you feel obligated to yourself.” For a while, Cerilli would charge one group more and one group less just to see if it impacted engagement. The more people paid, the more often they’d log in to the SinglePlatform system. Then he’d price correct later to make the overcharged group feel like they were getting a great deal.

5. Pinpoint the best delivery methods. Most people think that effective sales can only be conducted over the phone or in person. But this depends on the type of customers you’re going after, where your audience lives, and how they like to be reached. Make sure you test any unorthodox sales methods. See how emails perform versus cold calls. Test at what point in an interaction you should ask for the sale.

6. Test on a weekly schedule.“All of these tests you’re running can be affected by a lot of things — people’s personal lives, how many closes they’ve had recently, a string of particularly easy or hard targets, etc.,” Cerilli says. “You want to make sure you end up with the script that works the best under the most conditions. Also, don’t test more than one or two changes per repetition or you won’t know what worked.” After testing for over six months, Cerilli got to the point where he could close any customer over the phone. Only then did he hire other salespeople.

7. Adopt a “buyer’s mentality.”At Seamless, the sales team was struggling. Their tactics simply weren’t working, and Cerilli realized they needed to rethink their approach. What did they have going for them? They had many pre-formed relationships with big companies that used the platform to regularly order food. “When you go in with a seller’s mentality, you say things like, ‘Hey, it would be great if you signed up for Seamless. It would be awesome for you because of all these things…,’” he says. “When you go in with a buyer’s mentality, you say, ‘Hi, we manage the food ordering for Goldman Sachs, and we’re considering adding your restaurant to our system. We have some questions for you, so how about we set up a meeting?’” You have to dress up your assets and make your service something your customers want to buy. In Seamless’ case, they had a controlled market of consumers.

8. Don’t oversell. One major way people oversell is offering too many features. When you present someone with too much upfront, they don’t know what they're buying, and you’ll probably end up creating a crappy product, Cerilli says. “Stay focused and be great at fewer things — don’t be okay at a lot of things. You don’t want customers looking at some of your features knowing they won’t use them. Then they won’t agree with the price you’re charging.”

9. Design decks that keep the attention on you.“The deck we ended up with for in-person sales calls was mostly pictures and customer success stories. Successful sales people are trained to capture and manage customers’ attention. You don’t want to give authority away to the deck that’s behind you.”

10. Find a VP with solid individual contributor sales experience. People want to work for someone who has done their job before, who can set reasonable goals and understand their problems.

There's a reason so many professional coaches were amazing athletes— they already know how to win.

Hire and Train the Right Way

11. Start with 4 new hires. When you’re just beginning to build your sales team, you have to assume there will be a lot of churn. It’s a hard job, your product is new, and sales is high turnover on average. Half the people you hire probably won’t work out — even when you’re super picky about them. That’s the reality. So really try to hire in classes as you scale.

“I hear all the time managers saying, ‘I’m starting a new sales person this week,’ and I think, ‘One person? Oh my god that’s such a waste of time because they probably won’t work out,’” Cerilli says. “When you start out with four people, you’re much more likely to get one rock star and one B-player who can grow into the role.”

12. You want new hires to be young and hungry.“You want someone who has a bit of a chip on their shoulder — I call it Tom Brady Syndrome. He was drafted so late that he’s now out to prove what a great quarterback he is. Often, we’ll hire people out of Ivy League schools who don’t have that much to prove, so they aren’t that motivated.”

Looking across the 600 sales hires he’s worked with, Cerilli says the people who have performed the best are the ones who had paid jobs in college — who had to understand the value of a dollar from a young age.

13. Ask these three questions in every sales interview:

Did you have a lemonade stand growing up? “Believe it or not, 95% of the people I’ve hired had lemonade stands when they were kids. They were born entrepreneurs.”

“Sell me something that’s in this room right now. Make up whatever you want, but sell me the chair that you’re sitting on. Now tell me why I should buy ketchup instead of mustard. Ok great, now sell me mustard over ketchup.” These are the best questions for getting at someone’s innate creativity and versatility.

If there was a movie made about you, who would play you? What would your theme song be? What would you title your autobiography? “You can pick up so much about someone’s confidence and how they perceive themselves from questions like that,” Cerilli says. “You want someone who can think on their feet, be witty at the drop of a hat, keep you engaged.”

Wiley Cerilli, Venture Partner at First Round and Founder of SinglePlatform

14. Hire people for a 3-month trial period.“We chose three months because we knew there were going to be a lot of people who didn’t make the cut, and this gives you a nice formal endpoint to part ways. Also, it makes it easy to create an exact goal for that time period. Whether someone should stay or not becomes a quantitative decision.”

Just because employees are auditioning doesn’t mean they shouldn’t ask for help, however. “During this time, it’s actually expected that sales reps raise their hand so that their managers can coach them through calls or take over if they need to. That’s just fine. In fact, if someone isn’t seeking help like that regularly in the first three months, that’s a red flag.”

15. Put new recruits through bootcamp. At SinglePlatform, all new hires train for a week before making sales. Training includes everything from breaking down personality tests — so that they can tell what kind of customer they're talking to — to written tests, to listening in on hours and hours of live sales calls. “By the end of training, you want them to know exactly what to expect and how to handle the unexpected.” The last phase of training includes making simulated calls to their manager and other people at the company to see if they can sell the toughest audience.

16. Immerse hires in success. At SinglePlatform, Cerilli’s team plays recordings of successful calls on a weekly basis. “When you play them calls that were made by people they work with who got the sale, people start assuming that they're going to make the sale too,” he says.

Statistics show when you make a sale, the probability of you making a sale on your next call is way higher.

When people assume success, they go in with the confidence necessary to make it a self-fulfilling prophecy.

17. A and B players should be able to land 80% of their sales. “You don’t want C players,” Cerilli says. “So make it clear that 80% is a completely realistic goal. Even if someone is making a lot of calls and has a great attitude — if they don’t hit their number, they still don’t make it. No exceptions.”

18. Give quarterly bonuses, not commission.“You want to give bonuses on a quarterly basis, because every three months there are people who are leaving the company and you can save that cash. In the end, you save a lot of money. And especially when you’re at an early-stage startup, a quarter of commission or bonuses can make or break your company.”

19. Give people goals they can hit.“You can always raise goals as you need to, but it’s never good to lower them,” Cerilli says. “You need to gain people’s trust that you’ve set quotas in the right place. Do whatever you need to do to figure out this number, but good employees should be getting more wins than not.”

20. Have the script in front of people at all times.This goes for new and old hires. You want people to stick to what you’ve spent so much time crafting. “You understand what your real levers are and what’s working and what’s not. Having an exact script can be one of your greatest strengths, and when you train people well, it will come off as natural. They will be able to riff while hitting all the right points.” Cerilli recommends keeping the script as consistent as possible, with no more than one noticeable change a month. It also helps to print out a new version every week with any changes highlighted.

21. Teach hires to sell with customer stories.“You don’t want people using words like ‘I’ or ‘we’ when they are selling on the phone. No one cares why someone they don’t even know thinks this product is awesome. They need to talk about people their targets can relate to and why they love the product. You want your reps to convey why other customers believe the product is valuable. They can say things like, ‘I was just talking to so-and-so who you know the other day, and he totally loves this feature.’”

22. Fire quickly.For the first three months, you have the 80% rule in effect, and after that SinglePlatform enforces a two-strikes-and-you’re-out rule. “You have to fire a decent amount of people in this business,” Cerilli says. “That’s just how it is to manage and maintain a high performance team. It’s one of the toughest things about the job but you have to get good at it.”

Create a Robust Management Layer

23. Managers should closely track their teams. At SinglePlatform, managers are constantly listening in on their reps’ calls to gather intelligence, record feedback, and help them get better at closing deals. Cerilli recommends having one manager for every 10 to 12 sales reps so that they can invest enough time figuring out how to manage each person to success.



24. Make constant coaching practical.To make it possible for managers to monitor and help their reps, Cerilli’s team uses ShoreTel's M5 phone system. This allows the VP and managers to not only listen in on calls, but also provide real-time feedback to reps that customers can’t hear. It’s literally like having someone speak in your ear and provide advice like, “Hey, it sounds like they're still worried about X, why not try saying Y?”

Managers can keep tabs on the big deals coming down the pipe so they can come to their reps’ aid if necessary. “Usually managers will let reps know in advance if they are listening in, or they’ll come sit near them, or come sit next to them afterward to provide feedback,” Cerilli says.

25. Drive weekly one-on-ones with metrics.

SinglePlatform provides two forms that managers can fill out with metrics for each employee — including deals closed, minutes spent on the phone, as well as qualitative advice for how to improve. Putting information in this format tends to be less intimidating and gives people a concrete reference point for improvement.

“Plus the form gives managers structure — which is especially important for new managers who may be supervising their former peers,” Cerilli says. “They can look at the form and say, ‘Ok, first let’s talk about your closing technique…,’ they have more control over the conversation.”Here's an example:

26. Kick off Mondays on the right note.Cerilli and his team begin every week with a sales floor meeting where the focus is motivation. Account managers come in and read the “wow” customer success story of the week so that salespeople can hear the impact they're making for the people they call all day long.

“For a while we circulated these stories over email, but people just skimmed them. When they hear it in front of everyone they work with, it makes a huge difference. Now we try to pick a story where the customer was skeptical at first but got convinced by the end. That way, when everyone hits the phones, they won’t be so nervous about running into skeptical customers.”

The sales floor meeting also includes the “close of the week” — a recording of the most successful call from the previous week. Whoever made that sale is crowned king or queen of the sales floor. And yes, there is an actual crown.

27. Motivate with group competition.SinglePlatform runs all kinds of competitions for teams: Who spent the most minutes on the phone? Who got the most closes? Who is on the most consistent winning streak? “People get really into it,” Cerilli says. “They start fighting for their managers and it really solidifies loyalty.”

Create competition that encourages people to work harder but achieve together.

28. Make it fun. In addition to these competitions (which occasionally have themes like March Madness and Battle of the Sexes), SinglePlatform awards salespeople with big Legos for big sales and small Legos for small sales. “Now when you walk through the office, you see these big Lego towers, and its this really cool, easy way to identify top performers.”

Hone Your Process, Celebrate Your Wins

29. Build a SWAT team.It’s critical that you keep up with market trends and track your customers' needs. To evolve your script in the right direction, Cerilli recommends creating a SWAT team of 2 to 3 people to test out new pricing or pitches. “Run one large test a month,” he says. “And if it’s successful, expand the new script to 4 to 8 people, then to 10 to 12 people. Recently, we had two people test a model that pitched the value our mobile product instead of our network like usual. The response was unbelievable. One rep went from selling one and half licenses a day to 40 in a week.”

To make SWAT teams as effective as possible, don’t make the changes too big. Make sure it’s a realistic pivot from the script you’re currently using. You also want the team to be a cross-section of your sales organization. “You can’t have all your best people on your SWAT team because that would skew the data. You want one rock star and then one to two other solid salespeople who represent the majority of your staff.”

30. Celebrate victories everywhere you can.You want to communicate people’s wins constantly, as visibly as possible. Send out emails to the whole team. Acknowledge people’s anniversaries with the company and their sales milestones. Maybe they had the biggest sale of the week, the month, ever. Award actual prizes — whether it’s cookies or a day of go-karting. The more positive reinforcement you give them, the more motivated everyone will feel.

SinglePlatform uses a system called Hoopla to display the faces of people who just closed deals on screens around the office. The system even plays an anthem chosen by the salesperson pictured — a literal victory dance.

31. Celebrate the no’s too.“When people hit their first 10 no’s, we’ll ring the bell and celebrate that too,” Cerilli says, harkening back to his days hawking coupons. “Part of getting people where they need to be is getting them past that fear of rejection. Making it less scary and more acceptable is huge.”

32. Promote from within.This serves several functions. First, you know you’re creating managers that share the philosophy of close monitoring, constant feedback and keeping morale high. By making them mentors for reps and new hires, you’re only refining these details that make your organization successful in the first place. Second, when you hire from within the team, you send the message that you reward hard work and results.

Build a Great Environment

33. Make your office a place people actually want to work.Last year, SinglePlatform was named one of Crain’s Best Places to Work. But this was no accident, Cerilli says. In order to get the most productivity, you have to carefully engineer an environment where people are happy first and work hard second. This is one reason the company has enforced a strict “No Asshole Rule” from the very beginning. “We fired top performers because they didn’t fit our culture,” he says. Negativity and a bad attitude are contagious.

34. Bring customers in as much as possible.This doesn’t necessarily mean inviting them to the office, but it does mean telling their stories so often that they become a significant presence.

You want your people to know their customers are winning.

To this end, managers at SinglePlatform not only circulate customer success stories over email, they also issue a monthly report that everyone reads showcasing the top 10 to 20 accounts that are having a great experience with the program. “When salespeople see and hear customers saying things like they love the system or they logged in 200 time last month, they start believing in the product more, and they can sell it better.”

35. Start a meaningful speaker series.A lot of companies bring in outside speakers, but attendance is often weak. To make this experience more meaningful, Cerilli focuses on bringing in CEOs of other sales-oriented companies who will talk about their struggles not only with sales, but account management and tech issues. “Hearing from these types of people normalizes their environment and inspires people who may be struggling too.”

36. Run product demos early and often.Cerilli recommends bringing in representatives from the product team to demo new features or products on a monthly basis so that the entire sales org has the opportunity to ask questions, get up to speed on all the products’ capabilities, and truly understand sticky issues they may run into with customers.

37. Use lunches to connect sales with the company.Salespeople are easily silo’d at tech companies because they have such a different skill set. Ensure this doesn’t happen by formalizing cross-functional lunches. And give individual employees the chance to eat with executives from other parts of the company so they can better understand the mission and direction they're rallying behind.

The more you can connect salespeople to your company's values, the stronger they will feel about its success.

Turn on the Turbo-Boosters

Once you have your script in place, your training program turning out talented salespeople, and a strong layer of management, it’s time to scale operations to sell even more.There are two things you can do that will make a bigger difference than anything else:

38. Hire someone to do the hiring.At a certain point, it becomes unmanageable for the head of sales to be involved in every single hire. By hiring an in-house recruiter to do the sourcing and the screening, you streamline that process and feed an ever-widening pipeline of candidates to ultimately get more people on the floor and on the phones. This also frees up top sales management to think more strategically about scripting, who should be promoted, and what your SWAT team should focus on next.

39. Hire someone to do the training.Teaching new people — especially the young, less experienced people who eventually make the best reps — is extremely time consuming. If you think about everything SinglePlatform does to get recruits ready for sales calls, it requires someone designing and administering tests, running all-day programming for a week, setting up simulation calls, and providing granular feedback. If you can hire someone with teaching experience who really gets what you’re trying to do, you can free up many managers’ time and end up with a better trained salesforce, Cerilli says.

At the end of the day, your human capital will always be your biggest needle-mover in sales. The best thing you can do as you enter hyper-growth is find people who can focus on optimizing this one component. If you give people all the tools they need to win, they will.