How to Stage a Mutiny in Sales...That Your Boss Will Thank You For

A fireside chat with Kris Hartvigsen at Dooly

Sales teams are notoriously hierarchical. Customer Success teams might be a bit better, but they're still run in a top-down way. Dooly -- which just raised a Series A from Lee Fixel at Addition, Boldstart, myself, and a few others -- is turning that hierarchy on its head. Dooly is a “connected workspace,” AKA collaborative notebook, that simplifies the admin work for revenue teams, from notes, to pipeline updates, to to-do's. It's grown like crazy among the sales reps and CSMs who are tired of being asked to input information into various enterprise systems after calls.

CEO & Founder Kris Hartvigsen and I chatted the other day about his rebellious philosophies on go-to-market teams, and his own go-to-market strategy in approaching them. What became clear is that a rebel from Canada used Silicon Valley's own product-led growth tactics to disrupt the status quo of how Silicon Valley companies are run.

What motivated you to start Dooly?

When I was an individual contributor in sales, I found that an inordinate amount of my time was being consumed with administrative work that took me away from being in front of customers and working my deals. Reps live in two very different modes: their $50-an-hour mode and their $10-an-hour mode. Like most reps, I spent more than 60% of my time in the $10-dollar-an-hour mode, which was a terrible misuse of my time given that wages are always paid out at the upper rate. And much of the low-value time involved updating my manager and others on my customer meetings. Although it had to be done, I hated that admin work.

My co-founder and I started Dooly with one question in mind: What if we could make it so that your notes had a bunch of superpowers that would allow you to focus on your $50-an-hour mode as opposed to doing all the horrible $10-an-hour administrative work after you finished your meeting?

We also thought about the manager's perspective on sales meetings. When I was managing teams, I would often coach my reps while they were leading customer calls by writing on the whiteboard -- for example, what to say when an objection came up. But as a manager, I can't be on every call, which got me thinking, “What if I could build a product that could coach my reps in real-time?” Dooly does that and it’s been a powerful difference maker for the thousands of reps using our platform everyday.

What contrarian insight do you have about salespeople?

Most software in the sales org is bought with a top-down mentality, focusing on the shiny report...the outputs for executives. But Dooly gets discovered and distributed from the bottom up by reps that are frustrated with the ridiculous inefficiency behind those platforms. We’ve created a cult following -- an army of Dooligans. 

What we're doing is really rebellious. We're asking reps to go to their boss, tell them that the current tech stack doesn’t take their needs into consideration, and then tell them that our platform has changed their life, which in turn is going to change their boss’ life. Essentially, we’re asking individual contributors to stand up for themselves! And they're doing it.

Our users spend 2.5 to 5 hours per day in Dooly. Good luck finding a salesperson that looks forward to spending that much time in [insert name of an enterprise application...because they all suffer the same challenges!]. The average user saves between 5 and 12 hours per week because of Dooly. 

More than that, we’ve found that people will literally quit their job if you take Dooly out of their hands. Yes, this has actually happened.

If you're a manager and you're reading this, think about the cost of a cup of coffee every week to listen to your employee grumble about the frustrations that they have with [insert enterprise application] because it doesn't work the way that they work. You can take that cost of coffee and invest it in actually helping your team member perform, because Dooly costs less than 30 dollars per month.

I believe that salespeople have a really bad/misunderstood reputation in organizations. Folks think that salespeople don't put information into the CRM or communicate with others across the organization because they're lazy, arrogant, entitled, or ignorant. My belief is that they're actually dying to be collaborative and to have support from the rest of the organization: anything that makes a paycheck easier to earn and grow is a worthwhile endeavor. But without that support they will resort to their own devices, because it's simply the most efficient way to get shit done. Dooly helps reps collaborate with others for their own benefit and to the benefit of the rest of the company.

Are other teams besides Sales using Dooly?

Customer Success teams often use note-taking templates aligned to their client cadence. Much of our product roadmap caters to CS teams, and it makes sense to do so because there’s such a beautiful and obvious virtuous loop between sales and CS. 

One of CSMs' biggest frustrations is the hand-over from Sales, which has historically been garbage. So CS has a vested interest in getting Sales to use Dooly -- CSMs can more easily inherit the notes from sales calls. 

I was just talking to a company the other day that had furloughed a huge chunk of their employees due to the pandemic. They had to redistribute a bunch of accounts to the remaining team, who then had to reach out to all of the newly inherited companies to ensure they could retain the logos. But for the vast majority of the accounts, there were no notes. Imagine talking to two hundred different companies over the course of a few months, and you have no historical notes. "I know we've been working with you for a long time. I know you spent four million dollars with us. But I don't have a good handle on what we’ve done with you so far, so can you just get me up to speed on why you spent all that money and what you were doing with the product?" What a terrible experience. Behind every story like this, there's a churned customer somewhere. 

What's been your hardest challenge in building the company?

There are many. On the personal side, my father was quite sick for two years and unfortunately he passed away in September during the pandemic. Being a CEO is already a pretty lonely job. Being a CEO who's got an ailing parent is exceptionally lonely. 

We're a Canadian company and had to crack through the glass to get to where we are. Actually, as Canadians we like to say, "breaking through the ice." We had to work hard to build our street cred with investors. That in turn helped us attract great talent, and those new hires made it even easier to attract more great talent.

When we started out, we were ahead of the game. The market was still transitioning from enterprise-y applications. That presented a challenge, but we stuck to our guns, and it turns out that was the right move. The pandemic has underscored our value by making teams more remote, which makes data wrangling that much harder. We welcome the end of the pandemic, but are grateful for the metamorphosis to remote teams...it’s long overdue.

What roles are you recruiting for right now?

The easier question is “what role aren’t we hiring for right now?!?” We’ve recently hired our VP of Product, whom we’ll be announcing shortly. It’ll make a lot of noise, as will our new VP of Revenue, Michelle Pietsch, the former VP Sales at DataDog and Drift. What we’re keen to find are complementary talent in Product Design (ideally someone who has built an app with a hands-on experience and workflows to simplify user tasks), and a VP Operations to manage much of the day-to-day within the business. We’re always hiring engineering talent, and the same is true for sales, marketing, product and design!

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If you’d like to learn more about Dooly's approach to empowering sales reps and CSMs, check out https://www.dooly.ai/.

If you’d like to learn more about the Product Design role at Dooly, apply here. For the VP Operations role, email Kris at kris@dooly.ai.

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