The Sales Playbook That Turbocharged Outreach from $0 to $200M ARR

Nov 15, 2022
The Sales Playbook That Turbocharged Outreach from $0 to $200M ARR
Interested in reading more?

Sign up for our Enterprise Weekly Newsletter.

We'll send you our top, curated content straight to your inbox (along with top industry news, events, and fundings).

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Our November NY Enterprise Tech Meetup focused on a topic we’re particularly passionate about at Work-Bench: enterprise sales and go-to-market tactics. We welcomed Mark Kosoglow, CRO at Catalyst and former SVP of Global Sales at Outreach, to share the inside scoop on The Sales Playbook That Turbocharged Outreach’s Sales Process.

Behind this glamorous title was a lot of hard work. Mark joined Outreach as its first employee and played a key role in making it one of the world's fastest-growing companies, now valued at $4.4B. Mark grew the sales team from one to 150+ and revenue from $0 to $200M+ in ARR (he sold $1M in his first six months!). Now, he’s the CRO of Catalyst, a NYC-based Customer Success platform with over $65M in fundraising from Accel, Spark, and Work-Bench and customers including Braze, Heap, Fivetran, Attentive, and more.

Mark dove into how he grew Outreach's revenue organization methodically at every stage of the journey - check out our recap below and the full recording here

The Race to $1M

In the earliest stages of building a company, the sales process is a grind, so you have to find people passionate enough to stick it out and who can lead with grit. 

For Mark, this meant someone who loved sales as much as he did and didn't mind putting in the time to analyze what's working and what's not, and then teaching it to others on the team. For example, Mark recounted how he used to work with a credit card company where his sales role required him to cold call 100 people within 4 hours a day. He remembers successfully selling to four out of every 100 people - that’s 96 “nos” a day and almost 600 “nos” a week. But Mark didn’t let the “nos” affect him and used it as fuel to get to that one “yes.” This is the attitude that early-stage sales reps need to grind to $1M ARR because if you're scared or avoid the “nos,” then you’ll never figure out how to get the “yeses.”

For Mark’s 5 top sales strategies at this stage:

Read more on LinkedIn here.

Creating an Outbound Machine from $1M to $10M ARR

Most companies die during the run from $1M to $10M. But during this time, Outreach had already found its GTM fit and Mark was approved to scale the sales organization from one (just himself) to eight (four Account Executives and four SDRs). But what was unique about Mark's hiring process is that he didn’t hire tech people. Instead, he focused on hiring good people who he knew would work hard, remain loyal, but above all else, be able to showcase passion for the product.  

“I do some crazy shit. If you do everything like everyone else does, then you just add to the noise.” 

As the sales leader of the organization, Mark instilled some early and open policies among his sales team:

  • He stayed the best seller and led with founder-level excitement: Mark still thinks he sells Outreach better than anyone. Even as the leader of the sales team, he wasn’t above getting on a sales call to keep his sales game sharp. This excitement should be infectious to the rest of the sales team, and then passed on to prospective customers. 
  • Sales reps shouldn’t be afraid to be open and honest about their weaknesses: This allowed Mark to navigate the best ways to help his reps, further driving their loyalty and an overall smoother sales process. 
  • Sales reps should be mature enough to be self-sufficient: Mark firmly believes in trusting who you hired to do their job. So don’t micromanage. This allowed Mark to spend more time focusing on other aspects of the growth vs. listening in to discovery calls every hour and reviewing every outbound email. 

In terms of product marketing, Outreach didn’t have any kind of marketing engine for over a year. Mark sourced almost every deal outbound using Outreach and didn’t wait to hire a product marketer to unify messaging. Instead, he saw this as an opportunity for his sales reps to pick and choose what they were most passionate about the product and speak to that with prospects. While all messaging had to lead to a central product value, truly refined product messaging came much later. 

How “We F*ed Up” from $10M - $30M ARR

Scaling to $10M ARR very much felt like following a blueprint to Mark - hire incrementally and sell, hire incrementally and sell, etc. He thought that repeating this blueprint would continue to help the company grow exponentially. However, Outreach didn’t have the infrastructure in place to best continue this blueprint at scale.

For example, Mark hired a bunch of sales reps in North Carolina. However, Outreach didn’t have enough enablement people or tech in place to support them remotely, slowing their ability to ramp up and be effective sales reps. 

“There was a period where we had 100% turnover. What worked getting us to $10M, didn’t work getting us to $30M. So we had to change the blueprint.” 

So the team set out to hire more sales reps concentrated in the office, a product marketer, and an enablement person. Together, this team was able to support new hires and the company was able to establish and perfect a scalable sales process. 

Smoother Sailing from $30M to $100M ARR

At this point, the main focus was hiring people who could follow the established sales process.

“To get to $100M, we just had to make sure not to break anything.”

Some Wise Words on Selling Into the Enterprise

“Enterprise sales is probably one of the hardest jobs you can do. Enterprises are political machines bent on not purchasing stuff. So [sales reps] need to overcome that inertia of doing nothing.”

Are your sales reps dedicated to winning that company? Remember that enterprises are very siloed organizations and often very political among ranks and teams. The sales reps’ job is to navigate those intricacies, expose pain points, and insert the product into those pain points where possible. Mark recommended aligning your product to a specific initiative versus project. Why? Enterprises have 1000s of projects happening at any given time - these are already in the works and likely won’t get approval to onboard new tech. However, broader initiatives are always looking for things to help(make it cheaper, less risky, more efficient, etc.). 

Mark’s Best Bonus Sales Tactics

Narrative Demos: Mark spent about four to five months doing over 100 demos before realizing the demos weren’t resonating with prospects. So he thought, “there must be a better way to demo.” Most sales reps do the “click, show, tell” method in which they just information dump on a prospect during the demo call. However, prospects don’t care about information. What they really care about is finding something they believe will solve their biggest problems and the best way to do that is to tell a story. Mark would walk through a typical day of a sales rep without Outreach and then with Outreach. The purpose of this exercise wasn’t to necessarily close a deal, but to create belief that you can solve their issue and move the sales process forward. 

Master 5 Decks: Given sales is a transactional business, it’s largely science. Mark believes if you methodically present each deck below (in order and only with that deck’s specific goal in mind), you will win at a much higher rate. 

  1. The discovery deck 
  2. The demo deck 
  3. The negotiation deck 
  4. The information deck 
  5. The onboarding deck 

Interview Questions: All sales people can answer softball questions (if they can’t, they definitely shouldn’t be in sales). So it's important to identify the top things your company values and interview benchmarked against those. For example, Outreach values work ethic, ability to transfer passion, and coachability. However, instead of simply asking “are you coachable and tell me a time you displayed coachability” (again anyone can BS this), Mark believes in taking real world, physical cues. For example, he likes to give a candidate a role playing experience, then give them live coaching/feedback, then ask to do the role play again. Excellent candidates should be leaning in and taking notes, then display the feedback in the second role play. 

If you’re an early-stage enterprise founder or operator — connect with us directly to chat about anything GTM or check out our events page to stay in the loop on all things happening in the Work-Bench community.