Are You an Outlaw? Meet Samantha McKenna

Who has redefined what it means to think outside the law (aka OUTLAW) and is helping each of us in the process?

Meet Samantha (Sam) McKenna, an award-winning sales leader with more than a dozen years of experience in sales and leadership in the SaaS technology and law firm space. She has advised over 100 organizations on such processes and has also led global sales teams across large and medium businesses, including LinkedIn and ON24.

In her career, Sam has created over a dozen company initiatives, including onboarding, enablement and training for global teams, and has created programs around mentorship, demand generation, coaching and culture that still exist today.

She has won awards such as MVP executive, and also holds multiple recognitions for Rep of the Year and multiple President’s Club across multiple companies. She has been named a Top 50 Women in Revenue by SalesHacker and a Top 50 sales leader by Outreach.io. She actively speaks globally on the topics of women in sales/tech/leadership, and also on #samsales tactics. Most recently, she was featured at SalesLoft’s Rainmaker Conference on the mainstage regarding social selling, and has been a guest on nearly 100 podcasts and webinars, including Outreach’s Unleash 2020 virtual conference and LinkedIn’s “Live with Sales Leaders”.

Sam has also authored over 100 articles covering sales, legal practices and content marketing, and is the founder of the hashtag #samsales, which publishes sales hacks and best practices, and has north of 10,000 followers. She has also spoken at over 50 industry conferences such as keynoting sales conferences, speaking at sales kickoffs and leading workshops at partner retreats.

She is a graduate of Florida State University with a Bachelor’s in Business Administration, is originally from Geneva, Switzerland and is an active philanthropist in the Washington, D.C. area.

We asked Sam a few questions, and her answers can be found below. Enjoy getting to know this Outlaw!

Q: Where would you like to live?
A: I'm going to need a lot of money for a lot of homes...I have a deep love affair with Washington, D.C. and don't see myself ever leaving the area for good. But if I could have a few part-time residences, I'd start with Gstaad - it's where my grandmother had a home, where my parents were married and is close to where I was born and grew up, in Lausanne and Geneva. A place in Paris for chocolate croissants every morning, to be close to the rest of my roots and to read outside at cafes when the pink light hits, and a spot in London as well. For starters...

Q: What is your idea of happiness?
A: The freedom to run my own company and to be of help + positive impact in any way I can. Is that the cheesiest answer you've ever heard? Being of help will always fill my heart, but to do something that directly impacts my clients, which is what I'm paid to do, and then to see if pay off...there's no feeling quite like it. Their small wins, their closed deals, their "I followed your advice and it worked!!", the power of being able to connect two people who can be of benefit to one another...there's no feeling quite like all those rushes that come with doing this line of work.

Q: What is your motto? 
A: The Urgent Bird Gets the Worm. I'm all about urgency - I respond quickly, I talk quickly, I drive (too) fast, sometimes (often?) I speak before I think - zoom zoom, let's go :)

Q: Finish this sentence: “If I could have one super-power, it would be…”
A: A British accent. That's it. Okay okay. To cure the ill. Too soon? To teleport. I hate traffic and I love to travel. 

Q: What got you into working in the legal industry?  
A: I fell into the legal space, just like I did sales. I was an account manager for two years, and then was (unwillingly) promoted into enterprise sales by my then CEO. And man was I panicked - there's nowhere to hide when your job is to bring in net new deals. My CEO gave me a small crutch, that I could take five accounts with me as I went, and I took the time to evaluate the book of business I had already. Upon further investigation, we had some of the largest firms in the US working with us, three of which were mine and were Baker McKenzie, Hunton Williams and McGuireWoods. I took those three, plus two others, and called the CMOs of each firm to say, "Why do you use us? We're such a small company...why us?" Jim Durham was the first one who answered, and was my first CMO meeting ever (holy hell was I nervous). He told me it was the service that we gave the firm, which rang true for the other two, so I made legal a focus and grew those three firms into 43 in my next and last two years with that organization.