Making the Jump to B2B Tech Sales (Part 2)

It’s one thing to want to make a major career change. It’s another thing to execute it.

My journey from education to tech sales happened rather unintentionally. Because of this, it took close to 1.5 years to pull off.

(It doesn’t have to take you that long to make a similar transition, that I’m sure of!)

If you’re thinking about moving into B2B tech sales from another field, maybe you’re wondering: how do I actually do this?

A few things that allowed me to make the jump:

• An intro a former colleague of mine made for me to someone working in tech sales
• A relationship with that new contact that was cultivated over time
• A public demonstration of skills I would bring to a future sales role
• An opening at the company where my new contact worked
• Overlap between my past work and what was required of the posted role that made me a legitimate candidate

Let’s unpack each of these in more depth.

The Intro

If you want to change your career, you don’t need job applications. You need conversations with people who can help you get hired.

In my case, a former colleague of mine, Jess, knew I was building a coaching business on the side of my 9-5 (working in a K-11 school). While I wasn’t deliberately targeting a new role in business development, Jess thought I’d enjoy meeting her colleague who was leading sales at her current employer.

This guy’s name is Scott. It was early in 2020. (Yes, that 2020!)

The Relationship

Scott worked at an EdTech startup and was kind enough to jump on an introductory Zoom call with me. I wasn’t used to making “networking” calls like this, but ended up enjoying our initial conversation.

At that time, he was looking to hire someone with sales experience to his team. I wasn’t going to be that person for him, but we stayed in touch, having check-ins on Zoom once a quarter or so.

It was a natural thing to sign on to since COVID was keeping many people like me at home and quite isolated. Why not build some new social ties during these trying times?

The Demonstration

Over the course of the next year, I continued to build my coaching business, which meant I was posting content about my work and points-of-view in public forums like LinkedIn.

I was running another interview-style podcast at the time which kept my network growing and led to a number of leads being generated via referrals for my business. Slowly, I was signing new clients through a sales process my business coach had helped me implement.

In short, I was working on some of the same skills I use to this day as an Account Executive.

While Scott couldn’t see everything I was working on, he saw enough to know that I wasn’t afraid to hustle.

The Opening

Toward the end of 2020, Scott joined a different startup, managing the Sales Development Reps and providing mentorship to the broader sales team.

Around April 2021, he came to me about a role he was looking to fill at his new company. “You’ve always expressed an interest in learning about sales, Mike, I think you might enjoy giving this a try,” he told me.

Scott opened the door for me to interview with three of his colleagues in a series of 1:1 interviews. Here’s how that process went:

The Hiring Cycle

My first call beyond Scott was with the founding Account Executive of the company. He’d been with the company for a couple of years and remains a core part of the team to this day.

We had a great conversation, during which I confessed that I’d never really had any sales training (wasn’t sure if this was a deal-breaker or not at the time!). Between my work building my business, networking with employers as a career services advisor and a couple thoughtful questions I was able to throw his way about the company, he gave me the green light to meet the company’s CEO.

This was a scary moment for me. As humble as she is, she’s a businesswoman of incredible calibre and highly regarded within some of the most elite corporate circles on Earth. I felt nervous.

We had a rapid-fire 30-minute conversation. She looked through my LinkedIn profile during the first several minutes of the call, tacitly trying to figure out why Scott had brought me in for consideration.

Eventually, I made a breakthrough in the conversation. I connected the dots between the fact that she was looking for someone to sell directly to academics and coaches, and that these were the people I’d been working around for almost ten years. I knew their realities well and could speak to them like a peer (which is a HUGE asset in sales).

She left the call saying she had to “noodle on this” and that I’d hear back via Scott on possible next steps. In my mind, I had a 50/50 chance at the role.

I had one final 30-minute Zoom with the Head of Client Success. Briefly, CS is designed to be a proactive form of customer support and is largely responsible for client retention. Since I was theoretically going to be responsible for onboarding my own clients at Raftr (this never really ended up being the case), CS wanted a sense of what they were getting as a secondary member of their team.

This was a warm and fun encounter – kicked off by the recognition of our mutual love of Elton John – and we both left the call feeling excited by the chance to work together.

A few weeks went by and a Letter of Employment came around. I’ll spare the details of the brief negotiation period we had, though one thing to note is that our CEO pressed me to think hard about whether this was something I really wanted to embark on or not.

Start of a New Era

After reflecting, I signed the offer letter and joined the team. It was an exciting moment I remember vividly! My first day took place exactly 3 years and 2 days ago.

I’ll cover what happened from Day 1 until the end of Year 1 in the third and final instalment of this series before shifting gears.

Let me know if this has sparked any questions for you!