Women in Sales – The XX Factor with Pia Heilmann

women in sales pia heilmannWith so much talk about millennials in the world these days we decided we wanted to focus a few of our Women In Sales – The XX Factor posts on this generation as well. Our last post, with Jenna Cronin from VorsightBP was one of our most widely read! Thank you everyone!

For this post we reached out to Pia Heilmann. We met Pia several years ago and had the pleasure of hiring her on the Mashery SDR / Inside Sales Team in Boston. When Jim McDonough and I interviewed her we knew there was something special and we were both very excited when she accepted the offer.

Pia came in with great energy and an outstanding desire to learn. Needless to say she ended up being better than advertised. Once the Mashery acquisition occurred and we all started moving on to new and exciting challenges we were very excited to hear she continued working with Jim where they are both now at Attend

Pia, thanks for your insights, and welcome to The XX-Factor.

How many years have you been in sales?


Can you please describe the “aha” moment when you decided you wanted to be in sales?

Funny enough, I think my “aha” moment came years into my sales career. In all honesty, it is a career that I stumbled into. After years of listening to my father preach about the benefits of strategic thinking and tangible impact of marketing, the natural path for me felt like a career in marketing. The first job offer that was extended to me, however, was one in sales, and I accepted solely because I would be consultatively selling software to the roles that I ultimately wanted to be in (marketing and PR). Thanks in part to trial-by-fire, beginner’s luck, and good sales coaching, I outsold my first quota by over 500% and set a record within the company. The “aha” moment came months later when I started to apply sales skills to my real life–navigating social and family situations with succinct language and targeted questioning (using the real-life equivalent of a strip-line in a relationship with an uncertain future is surprisingly effective). I had a realization that I could make an impact, both monetarily contributing to the growth of a company as well as communicating effectively in all facets of my life.

What can you tell us about the single biggest sale you ever closed ($, sales cycle, company/ industry, etc.)

I think size of deals tends to be relative, largely dependent on target market, ASP, sales cycle, etc., so what I consider my biggest sale is going to seem small in comparison to others. My biggest deal was at Mashery selling a combination of API management and strategic services to an up-and-coming location services start-up. Admittedly, because our ASP was well into the 6 digits, it was a little deal clocking in at $60k, but it was a proud moment because I worked each facet of the deal, from prospect to social selling through to technical validation (okay, I got a little help with this one thanks to my friend Jason Parisi) and then close.

There are a few other deals that will always be “big” for me—closing my first deal ever in sales with my alma mater (Johns Hopkins University), recently at Attend with my other alma mater (Phillips Academy). It’s an amazing feeling to know that not only do you and your team have faith in the product you are selling and your selling ability, but established and reputable

Overall, though, my latest deal ($55,000) feels like the biggest, at over 10x our current ASP and historically the largest deal we’ve seen to date. Attend is a Series A start-up, so a deal like not only serves as a personal win but also monumental for the company–it proves that there is application in markets beyond higher ed, boosts our earnings for the Q, impacts the growth trajectory, and enforces confidence throughout the company. Not to mention, the referral for this deal was actually from a former BDR from the early days of Attend who chose to pursue a career in sports events.

Which women in sales do you admire most?

Now that I think about it, most of my biggest sales mentors are men. I tend not to separate by gender when seeking out best-practices or advice. I do follow Jill Konrath near-religiously and seek advice from Maria Cirino, a local VC and personal mentor with a deep background in sales and marketing.

If you could go back and give your early career minded self advice about a career in sales, what would that be?

There are two major pieces of advice that I fall back on when I hit a rough spot:

  1. I am independently wealthy, and I do not need your business. For those who have been through Sandler training, this may be familiar. Not only is it applicable to sales itself, but it also applies to career development and life. It gave me new respect for myself and to this day reminds me to pursue my goals in spite of detractors.
  1. You are selling software, not saving lives. While I am a big proponent of solution selling and feel confidently that the products I sell are a major value-add to the organizations I’m selling into, I struggle at times to not get personally attached to deals. I am most successful when I take a step back and understand that everyone has a life beyond their job, and the personal reasons for buying are often stronger than solely the value prop.

What advantages do you think women have in sales over men?

Depends on the market! When selling API management, my advantage was merely that I WAS a woman–the Architects, Engineers, and IT personas tended to be men working in largely male departments, so it seemed to be a breath of fresh air when I would call. I also believe that women are naturally more coachable, which is near-impossible to be taught but invaluable in a sales rep. Women also tend to have lesser egos which I think can get in the way for some men. Overall, I believe that both sides have advantages–it’s more about how you play to your strengths and understand your audience.

What advice would you give to men about working with women in sales?

I don’t think they need advice per se, though perhaps a reminder that women can be equally if not more so competitive and successful in sales. I think any good rep should welcome a challenge. For those men working with me, specifically, just know that I consider myself the most competitive in the room and will strive to be the top rep regardless of the challenges placed in front of me.

Wow Pia! This is amazing insight and perspective. Thanks for sharing all of this with us. Your stories are amazing and your wisdom speaks well beyond 3.5 years of sales experience. We look forward to following your career as it continues to grow and hope you will continue sharing your wisdom.

Social Stuff:
@pia_elisabeth / https://www.linkedin.com/in/piaheilmann
@rharris415 / www.theharrisconsultinggroup.com

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