Bushwhacking

It’s been 14 weeks since I got fired. If you missed the piece that I wrote about it, it’s here:

We're Letting You Go

Reflections on getting sacked:

I spent five quarters at my last gig. Nine months as a quota carrying enterprise sales rep and five months as a sales engineer.

In the nine months as a rep, I struggled. I worked to patch up an existing relationship that we were able to renew into a higher priced extension, but that was my biggest win.

The company hired a new VP of sales around ten months into my tenure. This guy was pitched as the mythical leader who would carry us from ten to one hundred million dollars in revenue. The idea that there are humans who can magically double or 10x your sales should trigger some healthy skepticism. Two weeks into the VP’s tenure, I was scheduled to have my first one on one. I stressed and lost sleep prepping for the meeting.

The question keeping me awake was, “how honest should I be?” My gut feeling was to give the full story. If I were in his seat, I’d want the truth. I reached out to members of my cabinet who said that I should not be fully honest if I wanted to keep my job. I needed to spin what was actually happening. Something like: “I know that my results are lagging, but here’s my plan to get out of it.” Show up with energy and solutions.

I ignored the advice. I went into the meeting and said “I am struggling. This is hard. Here’s why it’s hard. Here’s what we face as a team.” As soon as the words left my mouth, I could see his face change. I had just started the “how quickly can I get this guy out of here” clock. He didn’t want to hear the truth. He already had all the answers. It took him two tries to fire me because I’d built really solid relationships, but he was finally able to get me out the door in five months. He got gassed shortly after me.

Some lessons.

Sales is about storytelling. The story is a cocktail of fiction, aspirations, positive energy, and grand plans. It’s finished with a light dash of reality for garnish. If you want to be in sales (especially at a startup), you’ll need to sip this cocktail with customers and with the people who can fire or promote you.

If I was looking for a new job in sales, here are a couple questions that I’d spend time with. How long does it take to get someone’s signature on paper and how do we know when to start the clock? You need to ask these questions to three reps that do the actual job. Not the manager, not the revenue ops people, the reps. You’re listening for, “well, our CRM tells us that it’s 89 days, but I think it’s something different.” Dig for your own data. If the real sales cycle is 15 months, you can forget about the yearly OTE (on target earnings) on your offer letter. You’ll be making your base salary for the first year. And maybe that’s fine.

Here’s another. How complex is this sale? I don’t mean the technology that you sell. The tech is irrelevant. Does your offer solve a problem that can be explained in a sentence? Who buys it? How many people from the customer side get involved in the purchase? How many different teams or departments? Is the decision committee made up of members from third party organizations who have a stake in the outcome? You don’t get paid more for degree of difficulty. If you are looking for a job selling software, select the one that has a clear path to a signature. Not an easy path, but a clear one. In this job, we were selling to at least a dozen people, sometimes from three or four different organizations.

A final lesson. One that it seems I am destined to learn countless times. Once you’ve developed some hard earned experience, it pays to listen to your gut.

Now what?

Over the past fourteen weeks, I’ve tried to find a new path. I’ve been machete bushwhacking my way through thick brush looking for a little daylight.

I’ve collected unemployment benefits for any week that I haven’t earned any cash. During those weeks, I’m eligible for 900 or so bucks, which is the maximum allowed by law. This is the blood money; it goes to child care, groceries, car payments, gas, etc. This is half of what I was taking home. I’ve scattered other expenses across a couple of credit cards, and depleted any savings. An old friend handed me a wad of cash that I’ve made last longer than it should have.

My goal has been to fight through this period to find my own way. I’ve been trying to answer this question for decades now: can I make money AND do work that I care about? I still don’t know, but here’s what it looks like today.

Gigs. My work day looks like a giant quilt of mismatched parts.

My “podcast production company” has one customer, The Shift Group (https://www.shiftgroup.io/). I’m grateful for the chance to work with JR and his team. It’s been helpful figuring out some of this on the fly with a patient friend as a customer. We are getting close to releasing season 1. This batch of work will be complete with audio episodes, video episodes for YouTube, social media teaser clips, and blog posts. There is so much hidden work that goes into this. Finding guests, coordinating calendars, pre-show prep calls, building an outline/plan for the episode, fighting through internet connectivity challenges, post production work, and writing. I think what we’ve got is really solid. This is fun work. What I enjoy most is researching guests, thinking of the right questions to unlock compelling material, and doing the leg work to set everyone up for a great episode. It’s been fulfilling to work with my partner on this project, Evan (@evandesa on IG), a talented Toronto-based musician and audio engineer.

With the help of a dear friend from my last gig, I’ve networked my way to a freelance writing gig for a marketing company (thank you, LT). They send me a topic, I write 500-800 words on said topic, they send me some money. This work has been fun too. It feels a bit more like journalism. I read, research, find experts, hunt and gather material and then zoom out to try and write a compelling piece that makes sense.

A few weeks ago, another old friend called to see if I’d be interested in a work project. Did I want to help with a 6 week recruiting project to see if I can help them make a couple of key hires? I said yes because I love working with these people and I need the money.

Then there are the unpaid gigs that I continue to invest time and energy into. I’m here in this chair writing most days.

Closing thoughts

I’ve sucked at decreasing my monthly burn. It’s scary to notice how sticky a certain level of expenses can get. We work and reach and strive and struggle for the opportunity to nudge our expenses a little higher every year, which requires us to generate enough cash to shovel into the furnace. Capitalism baby.

I think summer in Massachusetts is a good time to try an experiment like this. The sun is shining and the days are long and warm and breezy. The neon death clouds of pollen are gone for now. On tough days, I can still go outside and feel the heat on my skin. The back of my neck is brown like an old baseball mitt.

On my best days, I have confidence in my ability to find work, and on lesser days, I think about the security of a W2. I’ve still got the machete in my hand and will continue taking hacks until I can’t any longer. If that day comes, I’ll dust off my best khakis and light blue Van Heusens.