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I remember when I first got into sales.

I was a eager 21-year-old, freshly minted Business Development Rep, and had no clue what the fuck I was doing. Thankfully, I failed fast and learned fast. And within a few short months, I was outperforming my peers.

Fast forward 3 years, I’m tasked with building a $10M Sales organization from scratch at a multi-national remote SaaS company. I know a hell of a lot more now than I did back then. And yet the knowledge gap between where I need to be to succeed is actually much greater than it was early in my career.

Helping Toggl succeed is testing so many of my cognitive, persuasive, empathetic, psychological and emotional limitations. It’s helping me see deficits in my own character that undermine my own success and the success of the organization as a whole. I’m 100% convinced that this is exactly the right opportunity for me, and I’m the best possible fit for the role I’m in..

First, I’ll document some lessons learned. Second, I’ll show off a bit because I’m an Enneagram Type 3.

Lessons Learned

Don’t work too loudly. Let your results speak for themselves.

Organizational change invokes fear and uncertainty. Communication is key to avoiding unnecessary conflict.

I missed 2/4 of my team’s weekly meetings. What the hell? One time I literally thought it was at 8AM but since they’re all in the EU it was 7AM. I was so pissed at myself. I set reminders on my phone 30 minutes ahead of various recurring team meetings to make sure I don’t miss them.

Be very careful and deliberate when setting expectations. People expect you to fulfill them. It’s best to communicate a desire to change expectations rather than fail to meet them and explain why after the fact.

Not everyone is a good fit for your product. The sooner you can get to “no”, the sooner you stop wasting time.

Criticism of your product isn’t criticism of you; it’s just a person expressing their dissatisfaction that they were unable to solve their problem. Take it in stride, thank them for their honesty, and deliver the feedback to the most relevant party.

It doesn’t take much effort to move the needle in a company. It just takes one strategic move with sufficient evidence to back up your claim.

People in other departments are excited to hear about the sales organization succeeding because they and see and feel the company (and their team, and themselves) succeeding as a result.

Nobody’s here to hold your hand. You’ve got to figure it out on your own. But people are more willing and eager to help than you know. Ask around, you’ll see.


I’ve successfully implemented the company’s CRM. We’ve got hundreds of thousands of ARR in the pipeline already, and we haven’t even been tracking leads for 2 weeks.

We’re turning on our semi-outbound engine tomorrow. Because Toggl has tens of thousands of new signups per week, it makes sense for us to enrich that inbound data and personally reach out to those who have manager/director/executive roles at large companies. Once that’s sorted out and Sales is handling that at-capacity, we’ll develop an outbound lead engine as well.

I’ve helped make it clear that to grow Enterprise Sales, we’ll need a Customer Success team – dedicated resources for high-ticket clients to know they’ll be fully onboarded and can reach out to with any questions. We’ll start building that out ASAP.

I’ve also helped make it clear that we need to centralize all outbound email communication on one central platform. I’m working inter-departmentally to make that happen via SendGrid. Check them out! Much cheaper than Pardot/Mailchimp/Marketto. As a result, the company has decided to put BizDev in charge of all outbound email communication outside of the Marketing Newsletter. Therefore, I’ll be redesigning our onboarding email cadences and optimizing for Sales conversions.

I also delivered a presentation at one of Toggl’s “Kitchen Talks” on the joys of improv comedy! I had like 6 people doing improv exercises with me. It was a freaking blast.

I will close my first sale for a modest $1,700 in ARR next week.

That same week, I might be flying to fucking Mexico to close the largest enterprise sale in the history of the company, meeting with the executive staff of a 16,000 employee division of a multi-national Fortune 100 company. Just a day in the life, ya know? We’ll see.