Making the Jump to B2B Tech Sales (Finale)

A good chunk of this story can be consumed in audio format by listening to the first episode of the Sales Seekers podcast.

You can find & subscribe to the show through your favourite podcasting platform.

---

Over the last few weeks, I’ve shared where my career was at before I transitioned into tech sales.

I also shared what the transition process looked like for me.

Now I’ll cover what happened in the first 12-15 months of my B2B tech sales career. This includes what I wish I’d known (good and not so good) before making the jump.

The Art of Onboarding

As with most jobs, my new role started with onboarding. It’s not uncommon for onboarding in a sales role to last a few months, but a few weeks can also be the reality as many companies want to generate new revenue as quickly as possible.

In large sales orgs, typically there will be a person or team (often known as “Sales Enablement”) responsible for onboarding newly arrived talent.

My training/onboarding period lasted a couple weeks and was carried out by my direct supervisor, a reflection of my organization’s stage of maturity. We were too small to have a dedicated enablement team (still are!).

My CEO had asked my boss to get me familiar with prospecting, one of the most valuable and important skills of a salesperson. While I learned a bit about our product early on, a lot of my focus was on what to say on the phone and what to write in cold emails when reaching out to complete strangers.

(What’s even more important than learning these two things? Learning about your prospective buyers – especially the priorities they typically have and challenges they typically face.)

Be Transactional!

I’d been tasked with selling our product to university & college professors in a high-velocity, transactional sales process. Being transactional is not something that comes naturally to me: I’m someone who enjoys investing in others and forming long-term relationships.

That said, transactional selling can be valuable to both clients (who want to quickly buy what they’ve decided they want) and an employer (who wants to generate as much sales momentum as possible).

Another benefit of running a transactional sales motion: you get to practice your craft a lot.. And developing your skills is critical if you want to be trusted with the big deals that pay out loads of commission.

I never really mastered this first assignment, in part because I prospected with too little regard for what we felt was our Ideal Customer Profile (ICP). You can’t help everyone in sales, but when you know who you can help the most and how, it’s a complete game changer.

Still, I managed to close business doing this new thing that no one else had ever attempted at our company. So when we pivoted toward exploring new markets to sell into half-way through my first year, I was asked to take the lead.

From Sales Rep to Project Manager

This is where my first year got both interesting and unique – most new salespeople won’t do what I did at this point.

As we moved into new markets, I essentially became a project manager tasked with creating marketing assets and helping our lone marketing employee write email campaigns that would allow us to gain some visibility and test the responsiveness of these markets.

I was getting paid to be an entrepreneur and build a business within our business. It was a ton of fun!

While this took me out of selling for almost two months, my effectiveness in this assignment gave my bosses the confidence to elevate my title and compensation to match all this responsibility they’d given me.

Just under eight months into my new gig, I was promoted and saw my earnings jump in a way that was unprecedented for me.

I was now officially an Account Executive and was expected to run longer, more complex sales cycles that would hopefully generate more revenue per client. It hadn’t occurred to me when I started that I could progress this fast, but it’s certainly possible in a startup environment.

Landing Clients 1, 2 & 3

Breaking into new markets is a challenge for any company. It’s doubly difficult for a startup that has limited brand awareness to begin with.

The first six months of 2022 saw me in many conversations with new kinds of prospective buyers. While it looked like we were going to land our first new market client in February, it actually took me until the end of June to get our first new logo outside our core market.

The second new partner came exactly a week later and was from the same market vertical as the first one. This felt like a huge triumph!

Signing these partners took a combination of:

• Our marketing surfacing very early adopters with either a mission-critical need or who were searching for a very unique product like ours, and
• Creativity by us to craft product packaging and commercial/contract terms that fit each of these accounts

Again, these things are fairly common occurrences in startups: less so in more mature companies with more clearly defined and tested ICPs.

Over the summer, I worked a deal that turned into our third new markets client in late September.

This one was a total record breaker for us. It was the largest deal we’d done based on two key metrics: Annual Recurring Revenue (ARR) and Total Contract Value (TCV).

(I didn’t hold these records for long: a colleague closed an even larger deal in Q4 of 2022. This is what you want to see in a startup!)

More important than records, our CEO was able to take this big new client acquisition story into fundraising pitches to investors, which helped us raise another round of venture capital in early 2023.

Final Takeaways

Like I’ve said, my first year experience in tech sales isn’t a common one.

At times, it was incredibly challenging. Going long periods of time between closing new deals can be damaging to a salesperson’s psyche.

But it was a year full of fulfilling growth which, as I said at the beginning of this series, is what I was seeking in my transition to tech sales.

In no particular order, some other takeaways from my first year in tech sales include:

• The smaller the company you join, the more flexible and adaptable you need to be
• When you sell for an early-stage company, you must find very early adopters in the market or you’re not going to close anything
• How quickly you can learn from recent experiences (good and bad) will usually determine how quickly you find some form of sales success
• It won’t matter how good you are as a salesperson if the product-market fit is weak overall. In other words, you have to be selling something that solves a meaningful problem that people will pay to solve. No pain + no willingness to pay = no deal
• You’ll never forget your “first” deals. Your first sale, first sale in a new market, first sale of a certain size – these are huge dopamine waves
• On the flip side, having a healthy dose of skepticism and controlled expectations when working with prospects can make it much easier to ride out the troughs in the waves. And there will be troughs!

That’s a wrap on this three-part series! Expect some shorter, faster-hitting material in the weeks ahead. As always, let me know what resonated or if you have feedback to share. 🙂