How DigitalOcean Turned a Team of 5 Sales Reps Into the Spartans from 300

how to transform sales reps

The interesting part amongst the majority of sales teams is that most of them consider their organization highly efficient sales machines, but in reality, they’re far from it. Most teams are simply filling “headcount” and then calling it “hyperscaling” their sales org. Teams like this grow from 1 to 20 to 200 to 1000… and then, ultimately, end up back at 200. From the outside, everyone thinks that a company who is hiring a lot or has sizable sales organization is doing well and they must be crushing it. Wrong.

Through our conversations discussing teams at scale, I mentioned to Richard and Scott how DigitalOcean has an incredibly small sales team with 5 reps total (our first group started in mid-February) yet we operate at the speed and effectiveness of a team that is twice our size. After speaking with dozens of sales executives and front line reps at much larger brand name organizations, it has become obvious that there is a common link between most of them: grow, grow, grow.

Sometimes this meant to grow at all costs. In reality, while most teams are focused primarily on scaling up, managers and directors should focus just as much on optimizing as they do on growing. Teams should grow, optimize, grow, optimize, and so forth. Instead of keeping your head down and trucking forward, look at the data you’ve collected during growth spurts, figure out what went wrong, replicate what went right, and take steps forward in the right direction. Sometimes that direction is not just the next step forward; it might be a step back to take two steps forward down the correct path.

During my conversations with these VPs and sales executives, we discussed their issues around not having adequate visibility into their sales process: it was incredibly difficult to ensure that the reps put the right data into Salesforce, adjust to new technology tools, and keep the team consistently organized in their overall approach. These conversations typically uncovered a never ending laundry list of a variety of reasons that all were leading to lost productivity and as a result, less time selling.

So, how do you find a solution for these bottlenecks when you have revenue targets to hit? The easy answer is to put another body on the sales floor and grow. I mean… if you put another person on the team, they’re bound to contribute to the overall team quota, right? Sure. It sounds simple, however it is way more cost effective to get 5 reps to each put up 20% more through optimizing their current role:

  • Eliminate bottlenecks
  • Obtain more qualified leads
  • Shorten sales cycles and/or improve close rates

It’s not an unusual thought process when you’re building out a new sales team to only worry about revenue, but if that comes at the point of sacrificing scalability and a playbook that’s repeatable, your sales team will hit a peak eventually and they’ll run into a brick wall. Once you hit that peak, the only way forward is down, and nobody wants to be Frosty the Snowman when his torso snowball is rolling down Mt. Everest. Hopefully this article will shed some light on how to build a lean but effective sales machine, how to capitalize on ROI opportunities, and how to get a different perspective on the opportunity cost of growing too fast, too quickly.

So, if you’re wondering how we did this or how to turn your team into the Spartans from 300, here is the short answer: make the right hiring decisions and be smart about how to optimize your process. Bring in a bunch of badass sales professionals who are passionate and care about your product and who– at the end of the day– love selling efficiently.

I’ll tell you what the answer isn’t  —  Account Based Sales.


Now, I’m not saying ABS (Insert Trendy Sales Process Name Here) isn’t the way to go (we definitely use that model here at DigitalOcean) but at the end of the day, it doesn’t matter what sales process you put in place, it matters who is implementing and executing that process.

Below is a breakdown of what I believe to be the foundational formula for success for any sales team that puts productivity first:

1. Leadership —

Think about who’s at the front of your sales organization. Do they resemble Leonidas or Xerxes?

UntitledAre they someone who leads by example at the front or are they someone who is in the back barking orders on a high chair? Do they walk around tossing a basketball and telling the reps to make a cold call but never picked up the phone themselves? That’s a huge, huge mistake if it’s the case. Don’t tell the reps to make cold calls, show them how to make an effective one.


2. Hire The Best —

Bring in people who really believe in your mission, are passionate about your product/service, and have a track record of giving it their all. Of course you’re going to want to look for all the standard traits of a good sales professional, but the number one thing to look for is people that are better (and smarter) than you. Surround yourself with people that can push and challenge you but who are also collaborative; after all, you are on the same team, trying to win the same business. You should never be the smartest person in the room and if you are, you should be worried.

If you already have a decent-sized team, take a good look at them. Would you say they look like anything like the team below? And no — that does not mean hire all males — but more on that topic in point #3.


Do you see any fat on that squad? Not a carb in 6 months.

In all seriousness, this photo represents trimming the fat and doing it quickly. Non-performers and negative attitudes are like leeches and you are only as strong as your weakest link. If you’re going to have an elite sales team, every single person counts. Have a full team of A-players and if not all members are at the same caliber of Kobe Bryant, then at the very least make sure they’re coachable. If your sales organization is a lot bigger and B-players are a more scalable option, make sure they have an A-player attitude. It’s a lot more worthwhile and a much better investment to turn a B into an A than put time into turning a C into a B. Always go from good to great, not worst to mediocre.

How do you ensure you hire the best? Structured. Recruiting. Processes. Don’t just go into an interview or phone screen and wing it. A structured interview process ensures that you’re vetting the candidate for all the right things. At DigitalOcean, the process has 6 stages:

  1. Recruiter phone interview
  2. 1-hr Google Hangouts manager interview
  3. Homework assignment
  4. On-site panel interview with 4 hiring managers
  5. Meet the COO
  6. Final round: meet the CEO

During that process, our team performs reference checks, and I’m probably (definitely) doing a back-channel reference check through mutual connections. And please, please do not try and do this all in an excel spreadsheet.

Use recruiting software like Greenhouse.io to help you manage the hiring process and Hired.com to find great candidates to fill the funnel. Minimize hiring mistakes at all cost because it’s a heck of a lot more expensive to fix one later. One of the best articles I’ve read on sales recruiting is from First Round Capital.

At the end of the day, people solve problems, not money; don’t keep hiring to grow fast because you think that it will help the team hit revenue goals quicker. Sam Jacobs, SVP of Sales and Marketing at LiveStream, made a great point in regards to this at The Sales Machine Summit last week during the session, “Building a Culture Optimized for Growth.” Jacobs mentioned how you should think about your sales team and its growth similar to a bus: don’t just fill the seats as quickly as possible– really think about who you’re giving each seat to and ensure that it’s the right person for the job.

3. Culture —

Think about how your team defines culture. Is work a happy place where everyone enjoys each other’s company and truly wants everyone else to succeed? Do people hang out outside of work? Do they hang out anywhere else besides the local bar? Think hard about your sales culture and what kind of experience you want to represent. Try to create an environment that actually drives real team culture in the day-to-day where people aren’t afraid to be themselves, are proud of their work, enjoy collaborating with others, and see a career path reachable within a reasonable timeframe within your organization.

Earlier this month, I leveraged our in-house Talent Development team to help with planning an off-site for the sales org. They were able to help drive team development, open up conversations about pain points that weren’t apparent to others, and have everyone take a look at things from a different person’s perspective. As a result, I can honestly say that the sales team has felt closer with a new level of trust that we’re all in this mission together. Inevitably, there’s going to be ups and downs but it’s about making the team realize that the grass isn’t always greener and the light at the end of the tunnel is going to be worth it. This was by far one of the best things I decided to do in my experience managing sales teams.

Dave Greenberger, VP of Sales at Splash, recently sent me a note asking if I knew any good sales ops candidates. I asked him if they should be junior or senior level and he said, “Doesn’t matter. Culture over everything.” To Greenberger’s point, you can teach skills (most of the time if it’s the right hire) but you can’t fix a bad culture fit.

Emmanuelle Skala, VP of Sales at Influitive, reported a situation where her reps cared so much about culture that one rep sacrificed a deal to help another rep out. They didn’t care about their quota (granted they were probably already there — it’s the thought that counts) but cared more about getting to the finish line together.

And finally: diversify, diversify, and diversify some more. When you’re building out a new team, make sure that everyone on the team has a different skillset. Don’t hire the same profile early on. Try to have all your bases covered:

  • 1 person should be the best cold caller
  • 1 person should be the best emailer
  • 1 person should be the best at social selling
  • 1 person should ______.

Let them feed off of each other and do not — under any circumstance — force a sales rep who isn’t good at calling, call. If they can write a damn good cold email, why does it matter how they get the demo? And lastly, don’t underestimate the importance of a good ratio of female to male ratio.

To learn more, DocSend has an awesome infographic with stats and data on how much better teams perform when they’re more gender-diverse.

While there might be a lot more male sales talent (at least in NYC), it is important to have female reps also. I literally just spent 20 hours sourcing for female candidates; ladies of the sales tech community, start referring your friends!!

Picture below to see how well we’re doing with that initiative:


One’s better than none! Shameless plug but reach out to me if you know anyone : )

4. Training —

Can’t stress this one enough either: make sure to have an on-going training program. At the bare minimum, have basic trainings set up (most teams don’t):

  • call trainings
  • role plays
  • email evaluations
  • shadowing, and more

The sales team at DigitalOcean does a weekly sales call training where the entire team listens to a sales call that was recently held by one of the reps. This helps build a collaborative, transparent environment that enables peer-to-peer feedback. In addition to that, we have a bi-weekly sales book club to propel reading something that helps us in our sales process. Our most recent book was The Challenger Sale and next on our list is The Sales Development Playbook by Trish Bertuzzi. All the knowledge necessary is nearby so create a learning environment where your team can absorb from a world where everything is now on-demand and instantaneous.

In addition to basic training and sales literature, we’re planning on hosting a 3rd party trainer soon (like John Barrows) to get a different perspective and help with efficiency amongst the team. Don’t put a dollar or budget on sales training when the ROI will speak for itself after a few deals. If you approach this the right way, your team should look something the below:


5. Sales Operations —

It’s never too early to fill your first Sales Operations role. A Sales Operations hire was the 6th person DigitalOcean brought on to the sales org and he’s been instrumental to our process. Sales Ops is integral because most VPs of Sales or early sales hires aren’t savvy with Salesforce. While they’re a heck of a sales person — they know how to sell and can sell bottles of canned air to someone if they tried — they’re coaches, leaders, recruiters, and do’ers. It’s rare when you get all of that plus someone who’s sales operations savvy and thinks about optimization, scalability, and has the ability to architect it all in Salesforce.

For this hire, make sure the candidate knows how to get their hands dirty, helps you implement all of your sales tools, runs continuous implementation, and continues to optimize the sales funnel. There’s a million things to do when you’re building out a brand new sales team and the last thing you want is to be stuck doing administrative tasks. Our Sales Operations analyst has helped us understand bottlenecks and we’ve been bucketing them into three categories on a regular basis:

  1. Automate
  2. Eliminate; or
  3. Outsource

Sales Operations is responsible for helping arm your team with the right tools to succeed, repair things when they are broken, and understand the optimal formula for success. If you think about it in the perspective of 300, sales ops (in that movie) was whoever helped them pick their gear for battle and gave them another perspective from the outside on how to prevent leakage in their formation.

By doing so, the soldiers were able to capitalize on having a lean team, leveraging teamwork as a solidified unit, and as a result, win battle after battle (spoiler alert – except obviously at the end when they lost because the little gremlin sold them out – buzzkill). Now, if the Spartans were your sales reps, their spears and swords would be the sales tools you use to arm them with and their formation/strategy would be your sales process/playbook. Once you’ve found the right people (soldiers), those are the two key important pieces to creating a high velocity sales team.

For DigitalOcean, we realized that most of the reps were going to be living in G-mail and Salesforce given our target market. Because of that, we set our reps up for success by utilizing tools like Outreach.io that lives wherever the sales rep are to allow them to be highly efficient while conducting sales activities.

In summary, you should really think more about optimizing your current process rather than adding to it. Instead of simply scaling and hiring more reps, it’ll save your company more time and money if you focus on leadership, quality of hires, culture, training, and synthesizing operations. You’ll also learn more and gain more experience along the way, setting you up for success in your career.


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    • 0
      @Eric Santos
      ( 0 POINTS )
      5 years, 3 months ago

      Awesome article Kevin!
      It was spot on some of the challenges that we’re facing with scaling our (now) 70-people sales org.

    • 0
      @Kris Jarvis
      ( 0 POINTS )
      5 years, 3 months ago

      I enjoyed your article, even from my marketing ops perspective. I’m always looking to find ways of making our reps more efficient from my side of things, I observe the team regularly and provide feedback to managers on what improvements can be made as well as recommendations on process/tools that can help. From every notification we send, down to the information we load into the system can either help or not so I’m always refining to find the right balance. Thanks for sharing!

    • 0
      ( 0 POINTS )
      5 years, 1 month ago

      – great post! Lately we have been discussing the most effective way to build a productive sales team. Your comment about establishing a good team culture is very valid and worth
      consideration for every B2B sales team. Thanks for your work.

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