What I learned building a sales org from the ground up

I had a decade of experience in growth marketing. In 2013, I became the first sales person at an early stage startup. Here’s what I learned in my first three months.

Finding the Right CRM for the job

I started out keeping track of students or “leads” on a spreadsheet, but soon realized I ought to find a CRM tool. We’d used Zoho at SoFi (much to the dismay of every person at SoFi who came in contact with Zoho), so I knew to stay away from that.

I had been introduced through a friend to the co-founder of Pipedrive, so I spent a day testing that out. I was really drawn to the visual way of managing a pipeline — dragging-and-dropping leads from one stage to the next. And as someone who wasn’t coming from a sales background, this struck me as easy and intuitive.

The obvious choice would have been Salesforce. Everyone was doing it. I’d worked with the Salesforce before, and (hindsight being what it is), I now know that a year later we did eventually embrace Salesforce.

But as an early stage sales lead — with a team of just me and one college hire — I realized that getting Salesforce up and running would be a tremendous burden — a steep learning curve I didn’t have time for.

Instead we chose Close.io — and it was one of the smartest decisions I’ve made. Close is a little less intuitive than Pipedrive, but very well designed, powerfully simple, and integrates mail-merge. In some ways it strikes me as the Apple of CRM tools — it strips CRM away to it’s core and leaves out a world of functionality that bloats Salesforce (and makes Salesforce so powerful in larger organizations).

Thanks to that decision, we had a CRM tool up-and-running with days rather than weeks, and we could get down to the business of closing deals.

Give yourself over to the machine

In my first month as a sales guy, I would grind every night, working my way down to that elusive inbox zero. And I would manually keep track of who needed following-up with. It was starting to drive me crazy, and I realized I would lose my mind trying to remember each lead before they fell through the cracks.

There’s a famous productivity author named Sally McGhee — she worked with David Allen (author of the Getting Things Done). McGhee’s productivity methodology talks about the simple idea — that tasks out to be organized in order of importance, and yet millions of us spend our day living out of our inbox — a list that is instead sorted in reverse-chronological order. It’s a tiny but powerful insight that’s stayed with me.

Eventually it hit me: there was no way to stay on top of all the correspondence. I had to give myself over to the CRM. We developed a system of buckets. A bucket for new leads. A bucket for leads that we’ve reached out to once. Twice. Three times. A bucket for after we have a good conversation. And my goal became to just move leads from bucket 1 to bucket 2. Rather than a top-down approach of trying to follow-up with individual people, my day became a bottoms-up approach of emptying each bucket at some regular cadence, and trusting the system to prevent leads from falling through the cracks.


Two years later, I have a team of four inside sales folks and three marketers. After a year using Close.io, we finally began bumping up against it’s limitations, and transitioned over to a much more robust (though cantankerous) sales stack using Salesforce, Marketo, and Outreach.io. Our bucket theory is still very much alive, and it’s still how we think about keeping leads moving through our sales funnel.

If you have a sales team of 1–2, and no one can articulate a strong reason you must have Salesforce, I strongly recommend Close.io. You can have it up and running in a few hours, it replaces both Salesforce as well as a sales automation tool like YesWare, and at an early stage startup, driving bookings quickly is likely more valuable to you than spending two weeks configuring a complex Salesforce instance and overcoming that steep learning curve.

Keep your sales process as simple as possible. As few stages as possible. As few fields as possible. You can always make it more complex later. Once you have the bookings to justify investing in better tools, you can easily migrate data out of Close.io into Salesforce. Just get something up and running. And start closing.


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