A ways back, I asked Brendon Cassidy, VP of Sales at LinkedIn, Adobe Sign / EchoSign, and Talkdesk to put together his playbook for double sales.  I thought it was a great checklist for all of us to take a look at.

Brendon wrote this post about his learnings about how he doubled sales once again in one quarter (the story of how he did it for and with me is here) a ways back at HackerRank, where he served as Interim VP of Sales.   But the list works just as well today and with others.

You may be different from Khosla Ventures and YC-backed HackerRank, but take his 8 learnings and see if you are applying the same methodology if you are in the $1m-$10m ARR band.  I think you’ll pick up at least one good idea or improvement.  — Jason, ed.


How We Increased Sales Nearly 100% In One Quarter at HackerRank  – Brendon Cassidy

For the past 18 months or so I had tracked the progress of a startup called HackerRank, and their founder Vivek Ravisankar, whom I met through a mutual friend.  I thought Vivek was one of the smartest young founders in Silicon Valley. As importantly, he was truly a good guy. What I knew of HackerRank:  a good startup that didn’t yet have great sales execution.

About 6 months ago Vivek asked me to come into HackerRank (I was consulting a couple days a week) full-time to be interim VP of Sales. The mandate: Put HackerRank on a growth trajectory that rivaled the fastest growing SaaS companies in the world. At that time, I was not looking to do anything full-time. But Vivek is one heck of a recruiter, and for me, the challenge of applying the principles I believe in again for a fairly short, consolidated window….seemed like a fun challenge, but a challenge. So I said I would give him 5 months, through the end of 2015, as the interim VP of Sales. HackerRank was not a $1 million or $2 million ARR business. They had significant recurring revenue and a lot of customers. This was not going to be easy.

The end result: In one quarter we nearly doubled new business and total bookings. In my book, none of these changes required any particular genius. Common sense. Just an FYI: I’ve done some iteration of this 4 times in early-stage startups. It’s worked every time. Bottom line: the focus needs to be on simplifying at every turn, driving strong black and white themes, and hustling 24 hours a day, 7 days a week. And making some simple but important decisions

Alright. Here is how we did it:

  1. Eliminated Traditional Territories. In my personal opinion, this is simply where most first-time startup VPs of Sales just get it wrong. It’s not always the right play, but 8 times out of 10 it is. And here is why: You have no idea what the territories are worth.  You don’t. You don’t have enough data. What’s most important is that salespeople have an equivalent opportunity to be successful. That’s a win for several reasons: A) It creates a sense of fairness while eliminating excuses. B) You create an apples-to-apples analysis of how good your team is. At HackerRank, which is a platform that assesses and ranks engineering candidates, there is a definite theme that 80% of the opportunity is in 20% of the territory. So having reps pound the pavement in Kentucky, Oklahoma, and Kansas is not the same as the Bay Area, New York, or Boston. At HackerRank, they had a traditional enterprise territory model. And not shockingly, the only reps who hit their numbers were the ones in aforementioned territories. Also: If you are expecting your AEs to do their own prospecting…stop expecting it.  Not unless your ASP is really high.
  2. Democratized Leads/Opportunities. This follows on the above. Once you’ve moved off territories — leads and opps can be distributed to the salespeople evenly from the SDRs, round-robin style. One might ask “well what about prospecting?” That we covered through our outbound SDR team, which does have geographic alignment. But once they get a meeting scheduled, that simply goes to the next person in the rotation, not the territory. In case you missed the memo, 99% of salespeople are terrible prospectors. And it does not scale to ask your AEs to create their own deal flow. However, those that can and do prospect, they have an advantage. And they can prospect into any company that lacks an existing opportunity. Remember: Someday you will return to territories. But It’s all about the appropriate structure for the appropriate stage.
  3. Centralized Around Inside Sales, Away from Field Sales. Our best salespeople were clearly on the ground in the Bay Area. Our remote field salespeople were literally closing almost no business, and yet we were flowing the vast majority of strategic opportunities through them. One rep told me on our first call “Everyone knows it takes 6 months to close a deal here.” UGH! So not what you want to hear. So, to me, it was a no-brainer to start moving our SMB and Midmarket AEs upmarket to handle bigger accounts because they were just plain better salespeople. As we managed out the field team, two things became clear: We started closing more business and we started closing it much faster. We did have one phenomenal field salesperson (in the UK). And the reason he was and is successful: He is superb. Any remote field sales hire in a startup who is less than superb (I mean elite, 99.99 percentile good)is going to fail 90% of the time. Again, this can and will probably change the bigger you get. Once you are post scale, once you have won your market and are a category winner, then you can double down on a field sales strategy. But not until then more times than not.
  4. Simplified Messaging and Pitch. HackerRank has a lot to show and sell, and needed to step back and lock in on primary themes and messaging. Which we did. Simplify our value points. Black and White. This helped a ton.
  5. Attached concrete, Agreed Upon Next Steps and Success Criteria to (Shortened) Pilots and Trials. Too often sales teams think that the pilot is supposed to do the selling for you. You have to do the selling. You have to create the urgency, the triggers, set the value. The trial does none of that for you. Oh yeah, we also limited pilot periods to a max of 30 days (from 3 months). That helped speed up sales cycles.
  6. Rebuilt our SDR Team with Less Reliance on Email and More Focus on the Phone.
  7. Moved to a Monthly Cadence instead of Quarterly. You can live on a quarterly cadence if you are Veeva or Betterworks or Workday. (Big ASPs and slower sales cycles). If you are everyone else you have to live on months, not quarters. And yes, it can be a grind. But it will positively impact everything. Enterprise deals close faster. SMB and midmarket deals close faster. It creates more energy. More urgency. More repeatability. And month over month growth. You can go back to quarters when appropriate, which is WAY down the road, btw.
  8. We Hustled. Every deal became an analysis of how to make it bigger and close it faster. Every month a sprint from day 1 to day 30. Every opportunity a chance to move the needle, push the envelope. We didn’t accept no for an answer. We pushed for reciprocity from customers and we held them accountable to their word. Understand one thing: Until you win, you hustle. And you do not stop until then. You hustle, hustle, and hustle some more. Until you’ve won.

And that’s it. HackerRank now acts, looks, and feels much more like a fast growth (even hypergrowth) SaaS company. They have a chance to win, and win big. However, the key to getting on the right path and sustaining it requires constant vigilance. You cannot lose your hustle. You cannot lose your edge. But better to have the issue of trying to sustain increased growth than not having it at all.

(note: an updated SaaStr Classic case study)


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