Episode Sixty-Seven

Turning Failures into Sales Successes

Guest: Cara Felleman, Director of Sales Development and Inside Sales at Resy

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About This Episode

Your latest failure might be dragging you down, but there are lessons within it that give you stepping stones to new and exciting heights.

But how can you take those failures, still painfully red hot in your memory, and turn them into lessons?

To find out, we spoke with Cara Felleman, Director of Sales Development and Inside Sales at Resy, a restaurant reservation platform.

Felleman believes that learning from failure gives you the grit and willingness to go the extra mile to put yourself in the best position to succeed. Previous failures prepared her to start her current job.

“I sat in a room with no resources, no phone, and no phone numbers in Salesforce with very little understanding of how turn-times affect revenue for a restaurant,” says Felleman. “I decided I’m going to make this work because I have the skill set. I’m just going to keep on the script and the process until it comes about. In our first year, my team generated $2.5 million. So I’m very excited about that.”

Why missing her first sales goal was a good thing

Early in her career, on the last day of a two-month sales training program, Felleman realized she was one customer short of her sales goal. She returned to work the next day knowing she would be fired. Instead, her manager put her next to the number one sales rep so she could learn from the best.

“I had to be a sponge, to listen to anything that was going on around me to learn from the best people,” recalls Felleman. “I would stay late and pick the brains of the people who were bringing in the most revenue.”

Questions to ask the top salespeople

  • What do you do? (How do you approach your job?)
  • Can I rewrite your script?
  • Can you roleplay with me?
  • Can you quiz me on prospect objections?

All of that work paid off. She went from “should-be-fired” to becoming the number three seller (out of 70).

Trust the numbers

Sales is a numbers game. You hustle to fill your funnel. At the end of the month, you see the results.

“The numbers don’t lie,” says Felleman. “The funnel is many small milestones. I need to make this many calls in order to get this many meetings in order to get this many holds (deal open but not concluded), and my close rate is X.”

By stepping back and looking at her funnel objectively like a math problem, Felleman put her trust in herself and the process. She just needed to work the variables in the formula.

“I knew that if I had 10 meetings, I could have five holds and one close,” said Felleman. “And then I got better and said, if I can tweak my close rate a little bit, maybe I could get 1.5 sales out of it.”

Constantly improving each element of the math helped remove the emotion that came from mean prospects who hung up or losing the deals you thought were in the bag.

“I think that’s probably one of the hardest things, removing emotion and trusting the process,” says Felleman. “Sales is a rollercoaster. You have good days; you have bad days. If you’re doing well, use that momentum to move forward. If you’re not doing well, don’t dig yourself in deeper. Just find that one thing that’s gonna get you out of that funk.”

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Failure Academy

When you fail, it is very easy to focus on everything you did wrong. That can be useful to a point, but it can lead to an obsessive negative spiral.

Salespeople are competitive and hate to lose. “If you have three losses in a row, you feel like there’s no light at the end of the tunnel,” says Felleman. “But what I try to focus on with my team is, ‘what went well in that demo?’ And they might say, ‘Well, I learned that this competitor has this feature and now I know how to sell against it.’”

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There is usually some good news with the bad, some metric that improved over the previous month. Use that metric’s momentum to improve it even more next month.

A successful sales manager’s role

Sales is about metrics:

  • Close rate
  • Hold rate
  • Meeting set rate
  • Call rate
  • Email rate

By isolating each of these elements, you can help a salesperson who needs coaching. A manager’s job is to identify the patterns for each salesperson, and the sales team as a whole.

It depends on your personal style, but the hardest part for many sales managers may be not micromanaging. Felleman believes you should let them come to you for advice.

“Sometimes you have to let someone fail so they have that realization that they want the support and help,” says Felleman.

Empathy is the key to building relationships with your sales team.

“It’s about getting to know them as a person,” says Felleman. “It’s not until you understand what makes them happy, what motivates them, what’s going on in their life, that you can be a good manager.”

Having that relationship with your team allows you to have important conversations in both directions. Felleman instituted a change in her sales department that the team didn’t like, and they felt free to tell her so. She was able to modify the change quickly to address their concerns.

Develop your own brain trust

You don’t have to go it alone. Reach out to peers. Talk it through.

“Luckily I have a very good network of friends and a lot of them are directors of sales.  We have a text group and we pick each others’ brains about all sorts of questions, whether it’s management or tech stack.”

Another sweet success for Felleman?

Emboldened to take risks, Felleman has just started a side company called Grateful Chocolates.

“I totally could fail; it’s a huge risk,” says Felleman. “But I also know the worst thing that’s going to happen is I’m going to learn a lot about entrepreneurship and starting a company in the food space.”

“Because I have had these failures early on in my career, I’m okay with failing. I’m not as scared,” says Felleman. “I embrace it because I know it’s going to take me to the next level.”

If you want to get in touch with Cara Felleman, you can reach her on LinkedIn, Instagram, and via email.

This post is based on a podcast interview with Cara Felleman, Director of Sales Development and Inside Sales at Resy. To hear this episode, and many more like it, you can subscribe to The Sales Engagement Podcast.

If you don’t use iTunes, you can listen to every episode here.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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