Confessions, Learnings and Insights From a First Time Sales Leader in SaaS

Stretch VP? Let me explain.

Just over a year ago, I moved into a VP of Sales role with a growing SaaS company. I’ve been in sales my whole life. My first sales gig was at 12 years old knocking on neighbors doors with my best friend and “co-founder” pitching our newly formed lawn mowing empire sure to take over the world. I knocked on doors selling satellites in the summer to put myself through college. Upon graduation, I landed a gig selling advertising which led to similar mar-tech sales gigs and eventually owning my own company before jumping fully into SaaS about 8 years ago. I fell in love with the concept, model and industry.

Fast forward to last year. As a new VP of Sales in SaaS with something to prove, I wanted make as big of an impact as possible, so I started to consume every podcast, blog and white-paper I could get my hands, ears and eyes on (future post on these later).

One of the more enjoyable, insightful and helpful podcasts for me is SaaStrstarted by SaaS Founder/Entrepreneur/Legend Jason M. Lemkin and hosted by “Teen-age Phenom” Harry Stebbings (Founder of The Twenty Minute VC Podcast– I think he just turned 20? Sheesh).

Lemkin references a term called “Stretch VP” quite a bit and that immediately resonated with me. I decided to own it. I’m a Stretch VP. Sure, I had founded and ran my own small business. At our peak, we had a little over 10 employees all reporting to me. But recruiting, organizing and running a SaaS Sales team — as a VP of Sales — was a new thing for me. Its huge being able to study other VPs of Sales and their struggles, history and insights. This was/is immensely valuable for me.

But I craved more. And I wanted to give back. I wanted to share my own hurdles and findings in hopes they may help other Stretch VPs in similar circumstances. But I was pretty convinced my voice didn’t matter or at least wasn’t large enough to make an impact. But I decided that little voice shouldn’t be listened to. I would allow myself to start ranting and raving even if no one was listening. Then it hit me- I don’t have to do this alone. I realized I have an entire network of other Stretch VP’s I was already talking with. We were going through similar things and often talking about them. I could assemble a team of Stretch VPs and have them share their own confessions and learnings for us all benefit from. This way, we could all continue to learn and share from each other’s findings.

So…I bought the domain, hacked together a basic website and blog and started Stretch VP.

My goal for Stretch VP is to be both an outlet and resource for discussion on growing sales for SaaS. Posts may not be a definitive roadmap on best practices, but maybe even a question or something I know others are looking for answers to. We’ll discuss issues with leading teams, recruiting, motivating reps, overcoming objections as well as tech stacks, hacks, hindrances as well as overall things we are all dealing with on a day to day basis as VPs of Sales. Sprinkle in comp plans, stock options, dealing with VC’s, fundraising, marketing tactics, business development, outbound/inbound, strategy, partnerships — and there should be an endless amount of content to discuss.

Are you a VP of Sales (Side note: I believe we are ALL Stretch VPs — future post on that later) in the SaaS space? I’d love to have you share your experience and insights. You can even remain anonymous as some VPs wished to do. Email me at: vpstretch (at) to get started. We’d love to have you on anyway we can get you. Currently looking for:

I hope you’ll join us in the process as we learn, grow and share. Stay tuned…

-Stretch VP

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