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Everyone in sales wants to know: What do the top reps in the business do differently from all the rest?

To answer this vital question, OpenView Venture Partners and InsightSquared hosted the first ever “Best of Boston: Premier Sales Reps Tell All.” This event featured a panel of the top B2B technology sales reps in Boston, including:

  • Taylor Grabus, Sales Executive at Datto, Inc., who has in the past year alone been promoted twice and exceeded his quota by 108% for 6 consecutive months.
  • Cesar Lara, Manager of the Opportunity Consultant Team at SmashFly Technologies, whose 7-year career spanned the roles of lead gen, lead gen sales team, and account executive.
  • Farrell McClernon, Channel Sales Account Executive at HubSpot, who previously co-founded the marketing software company Privy, building out the sales operations and executing a go-to-market sales strategy.
  • Donny Barnas, Account Representative at Logentries, who surpassed his quotas as a BDR at Logentries and was quickly promoted to New Business Manager and now to his current closing role.

These four talented reps shared honest stories about their personal challenges on the job, how they sell successfully, and how they’ve grown their careers. Here are 5 key takeaways from the event to help you improve your own sales career and learn from the best reps in the business.

1. Sell Like a Human

While reps on the panel specifically cited the Challenger Sales Model and the Sandler Method as guiding principles, they noted that reps can get so caught up in sales tactics they forget they’re a person selling to a person. McClernon said she focuses on building trust with prospects from the start.

“Many reps establish goals early on, but you also need to understand Consequences and Implications,” McClernon said. “What will happen if they don’t reach those goals? If they tell you they’ll have to lay someone off, that’s the real reason they’re going to buy. If you get someone to admit that, you’ve earned their trust and they’ll move through the process faster.”

Barnas said he allows customers to guide the selling process so they feel comfortable, rather than pushing too hard to follow a set path that may kill the deal.

“It’s OK to not be OK,” Barnas explained. “Let the customer say, ‘I don’t want to talk about numbers yet.’ I let them have that power, and it empowers them to make the decision.”

2. Learn from Your Peers

You should always be learning best practices, because sales is always evolving.

- Farrell McClernon

Especially at a startup or an SMB, sales reps may not always have the luxury of extensive sales training to prepare them for the job. Instead of trying to figure out everything on your own, Grabus said reps should turn to more experienced members of the team.

“At my organization, we take some time to learn about the product, but it’s really all about learning on your feet,” Grabus said. “We work in an open room and we learn from each other. If I hear one of my colleagues having a great conversation with an end user, I can learn from that.”

However, learning from your peers doesn’t only mean sales reps within your own company. You should also look for advice within the local sales community.

“We have a really great sales network in Boston, so get out there and ask people for meetings,” McClernon advised. “If you know people who are good at their jobs, ask them to grab a beer and try to learn from your peers. You should always be learning best practices, because sales is always evolving.”

3. Even Tough Experiences are Valuable

The reps talked about some of their toughest jobs and biggest professional challenges. Lara revealed his struggles selling life insurance, before he decided to move into high tech sales. However, he said even the worst experiences taught him something important for his next role.

“In life insurance sales, you learn fast how to deal with rejection,” Lara said. “If you think B2B sales rejection is bad, you don’t know how bad it is until you have to go to someone’s house and are rejected in person. I learned the ability to take rejection and let it roll off my back.”

McClernon talked about the challenges of working at an early-stage startup, where she was creating a sales process from scratch. She said you have to really understand your buyer in order to sell a brand-new product.

“At a startup, you’re making it up as you go along,” she said. “I combated that uncertainty by getting on the phone with a plan. Be agile based on what you hear on the call, but know what value that person is going to see in what you’re pitching before you even get on the call.”

4. Respect Your BDRs

You’re not there to be a dictator; you’re there to partner with your reps.

- Cesar Lara

The reps, many of whom previously worked in Business Development, discussed the relationship between Account Executives and BDRs. Barnas said BDRs should never feel like they’re at the bottom of the ladder and undervalued by AEs.

“Learn what motivates your BDRs,” he said. “I had one Account Exec say that he’d duct tape my headset to my head if I didn’t make more calls. I think my dials were in the single digits that day. Maybe some people like to be threatened, but that didn’t motivate me at all.”

Many of the reps were promoted quickly out of the BDR role because of their success. Lara said he faced the challenge of moving from a BDR to a team lead, and navigated the switch from being a friend and colleague, to a boss.

“Be humble,” he said. “You’re not there to be a dictator; you’re there to partner with your reps – you just have a different set of responsibilities now. If you have that humility, you’ll earn their respect.”

5. Be Honest

I live and die by being direct in my conversations.

- Taylor Grabus

These top reps agreed that sales should never be about manipulating your prospects, but should instead be an open and honest interaction. Grabus said he believes in the Sandler method, of being very honest and transparent on calls.

“I live and die by being direct in my conversations,” Grabus said. “You don’t have to come off as cocky or rude, but I prefer short, direct questions. I call out the vibe – if you see a conversation going a certain way, call it out honestly and say something to get them interested.”

This honesty will help you find out what prospects really need for their business – this should always be at the forefront of every sales reps’ mind.

“Sales is really about helping people solve their problems,” Lara said.

 

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