An interview with Jessica Menden, Senior Sales Director at a Customer Engagement Platform

You’ve been selling your entire career (over a decade). How did you get your start in sales? When did you know it would be your career?

I graduated high school in 2008, at the beginning of the bank collapse. Coming out of school with a degree in marketing and entrepreneurship in 2012, and having been focused on volleyball versus internships throughout my school experience, the job market was extremely tough. Most companies had cut their marketing budgets and teams as an outcome of the recession, and the potential to make a salary that would even cover my debt seemed impossible. 

I was constantly interviewing against people that had decades of marketing experience and masters degrees for entry level positions. It wasn't long before I decided to look at alternatives,  and started working with a career coach who gave me my first shot, selling copiers. Yes, people used to print things! I'll never forget her saying “This will be the hardest thing you’ll ever do. If you can hack copiers, you can do anything.” I knew this would be my career there and then. 

You’re a senior sales director. What advice would you give to somebody who wants to reach the director level? 

Be transparent with your goals. Talk about them frequently, both internally and externally,  quantify them (make them SMART). Be realistic, be coachable, and understand things don’t just happen overnight.

The biggest mistake I see younger people make is just not asking for what they want or need. This is not just in their own careers, but in the sales cycle too. If your company won’t take a chance on you, someone else will. Know your worth and what you want from your career. 

You played Division 1 volleyball and also spent 6 years as a coach. What are some of the skills from your time as a D1 athlete or coach that have helped you in your sales career? 

Coming out of school as an athlete is a very unique and challenging experience. It kind of feels like the first day of school again where your parents drop you off, and you go “ok, now what?” All you’ve known is eat, sleep, school and sports for 4 years.

It was difficult to articulate to recruiters exactly what you had been doing in college for 40+ hours a week. It frankly took a bit of time before I stopped worrying about having to do sprints if I screwed something up! 

If you boil it down, I think there are two core elements that make athletes successful sales people.

1) Sports and Entertainment are sales-driven. As an athlete, you essentially become a part of the sales process. You’re the product! As such, athletes really touch every part of the sales cycle without even knowing it.  Outside of the sport, a lot of time is spent working with the university marketing, sales and public relations teams. This gives athletes an early understanding of how internal processes work, how and why “products” are marketed, and how many of the internal systems it takes to accomplish what we see as the end product.

2) The intangibles gained from the highest level of athletics.  It takes strict accountability in all aspects of your life to achieve success. It takes vulnerability and courage to fail constantly in the public eye. It takes the highest level of competitive spirit to succeed at this level.  

What does a typical work day look like for you? Walk us through it. 

  • 7-7:45 Pilates
  • 7:45-8:30 coffee and Arnie (cute dog) walk
  • 8:30-12 meetings
  • 12-1 - Arnie walk and lunch
  • 1-5 meetings
  •  5-7 break
  • 7+ emails / catch-up 

Meetings range from customer calls, to internal forecast meetings, all depending on what that week brings! 

While it doesn’t sound very exciting, the benefit to working in sales is that you really do own your calendar. Some weeks you’ll be working 60+ hours, while others will be more like 30, (with a few rounds of golf). Both types of weeks are important if you want to have success and longevity in this career. 

What's the one thing you’ve found that helps you be successful in sales? 

I’ll give you 3:

1) Attention to detail. As a woman in sales, I’ve learned that not only do I have to be better than my peers, but I also need to be more thorough and knowledgeable than my customers at times. Do your homework, and when you think you’re done, do some more. I guarantee that one of the tidbits you pick up will be the game-changer between you and the competition. 

2) Understanding. The sales process is not about you, and it’s not really about the product. The sales process is about your customer. What are their goals? What are their ambitions? How does your solution improve their lives not just professionally, but personally? Transactional deals are done by filling IT requirements, transformational deals are done by building a plan and relationship that does more than fill RFP check-boxes. 

3) Confidence. Nobody knows if you’re lying if you say something confidently enough :) 

What are your long term career goals? Early retirement or future CRO? 

I kind of live by the mantra “if you’re not making money, you’re spending it.” I really can’t see myself ever retiring. However, eventually, I hope you’ll be able to find me in a small beach town where I own the local margarita joint!

Until then, I have a few ventures that I’m looking to expand, including doing some sales consulting and coaching on the side. So, maybe CEO, not CRO! :) 

Life is an amazing adventure full of ebbs and flows. Take opportunities when they present themselves. If you’re not uncomfortable, you’re not growing! 

Do you have any advice for people who are just starting out in sales?

Be unapologetically yourself.

85% of selling is based on trust, so if you’re going to be successful, you need to be authentic with who you are, and that’s going to look different for every one of us. Bringing your unique value proposition to the table can be just as valuable as any amount of expertise. Additionally, don’t be afraid to ask to know what you don’t know.

Sales can be intimidating, especially if you're new. But know there are no stupid questions. When you have more information, you’ll be able to better understand how to fit yourself and the product into the puzzle.

Finally, build your tribe early. Find people you admire in the industry, and find a mentor. The more people that will give you true, unbiased feedback on your approach, the better you’ll do in the long run.

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