Why I joined Drafted

Now that I have been asked this 100+ times I figured I would make this into my first Medium post.

So let’s run through the background, the dating phase and ultimately the commitment.

Background:

I started my career in newspaper advertising which may quite possibly be the hardest sale in the digital age. I did that because I knew it would be hard and if I could sell that product, selling anything else would be a breeze. After a few promotions at Gatehouse Media, I got an opportunity to be one of the first sales reps at Grubhub.com which was my first big win in a quota carrying role at a start-up. I had no idea it would grow from $100 million to a few billion while I was there and it really opened a ton of doors.

My first tough decision: Do I leave my shares of GRUB on the table when things were going great to take on a management position at a tech start-up in my hometown, Boston? The answer is YES, so I joined Leaf and I consider it the only time I have really fell on my face in my career. People are right when they say you learn much more from failure than you do from success. Although, some would say we received a successful exit in an acquisition for $20 million for a few years work. For the first time, I felt like I did not have all the answers.

My next easy decision, joining HubSpot. It was a pre-IPO company at the time with the promise of learning marketing and scaling a team where the product actually fit the market. I had never done enterprise sales before but, I knew I could sell anything. In a few short months I quickly moved up the leaderboards and I felt like I would be at HubSpot for the long run. We had a great product, amazing culture, great people and a brand name everyone recognized.

Hiring at Leaf was impossible and probably why we did not succeed. Hiring at HubSpot was also a challenge. Which is insane because it’s HubSpot. Why was it a challenge? Well, it’s a challenge at any company. It’s a great question and I think about it every day.

• Finding a sales rockstar that could also fit in our culture was not easy
• Did they understand marketing already? Could they master ALL the software? Did they know that making cold calls at an inbound company was the only way to smash quota?
• And probably at the top of that list, could we find people that would stay hungry in a very transactional monthly business?

All of these issues in the hiring process were often answered by referrals that we knew would be good before they even went through training. The problem was we just did not have enough RQLs (yes, i just invented “referral qualified leads”) to build a team off of referrals only.

And guess what led me to Drafted in the first place, a referral. When you work at HubSpot you get used to blocking out the everyday recruiters calling, emailing and spamming on Linkedin but, a warm introduction to talk about something a trusted friend knows I’m interested in? I will always take that call.

The Dating Phase:

The most difficult decision in my career thus far, leaving HubSpot for another start-up. What was I thinking? HubSpot is a staple in sales and marketing and I’d finally broken a few records and earned my place at the top of the leaderboard. Not to mention I had an amazing team that was my same breed and was also striving for GROWTH.

Those familiar feelings when I left Grubhub with 24 months left in my vesting cycle started creeping up again. Meeting the Drafted team was key and after a few face to faces I felt myself waking up energized and full of new ideas. I actually wrote 4 blog posts because I felt so passionately about the model and that’s when I knew Drafted was the right decision. Special thanks to my mentors who helped me make an objective decision after reviewing the pros and cons.

The Commitment:

Now when I slept on it for a few days, I started thinking about why would I leave and I saw an awesome meme about why talented employees stay at companies.

This was *almost* the meme, except one was “Learning”…

Learning and Challenged really stuck out to me and I realized I had completed what I came here to do, learn a lot so I can help people be better at their jobs. That along with the support of my most trusted advisors led me to calling Vinayak and saying let’s meet for coffee, I’m in!

What led me to saying YES:

1. I actually have experienced the pitfalls of growing a team
2. Referrals work, do not need to sell anyone on that
3. I wanted a founder who was the exact opposite of me. Let’s say an engineer and an MIT graduate could be considered polar opposite. Thanks Vinayak for meeting that requirement…
4. Hiring is the hardest, the most important and the most time consuming thing in growing a business. And this $400 billion industry has not been fundamentally disrupted since classifieds going online back in my newspaper days.
5. I want to build something. A team, a product, an ecosystem and most importantly a flagship company here in Boston.

“Referrals drive the world.” Vinayak Ranade, CEO Drafted

The recruiting playbook is broken, let’s re-write it together!