For the love of sales

I don’t think many children dream of becoming an Account Executive at a B2B SaaS start-up. Maybe a ninja, guru, or astronaut on a rocket ship, but a salesperson? This lifelong aspiration may be limited to a select few.?

The truth is, I’d been rehearsing for this career path without even realizing it.?

It's 2000, and I desperately want a dog, particularly a Bichon Frise. My father, the most formidable economic decision-maker in my career thus far, was adamant that we’d never get a canine companion. Rather than begging and pleading, I knew I had to be strategic. I needed what all great pitches require, a slide deck. I carefully crafted my pitch on my family’s turquoise iMac, utilizing research I collected from library books on dogs. Bichons are very cute,? hypoallergenic, and nice… Having a dog will teach me great responsibility, followed by a photo montage of Bichons and a promise to walk the dog, day or night, rain or shine. Unfortunately, this initiative failed, most likely due to my inability to uncover my father’s Pain concerning the lack of a family pet. But hey, we learn more from our losses than our wins.?

I hustled through college working at the mall, slinging store credit cards, waiting tables, and scooping ice cream, but nothing translated into professional skills that would make me employable in a highly competitive, post-Great Recession job market. It wasn’t until later that I realized those part-time gigs taught me invaluable soft skills like rapport building, time management, and strengthening my EQ.?

Upon graduation, with my state school archaeology degree in tow, I worked as a daytime bartender at a sushi restaurant near a Marine base in North Carolina. Eventually, growing frustrated with returning home every night covered in spicy mayonnaise and Bud Light, I decided to pursue a radical change in my life. I crafted a resume, made a LinkedIn profile, and applied for every Manhattan-based entry-level job on Indeed. I didn’t know where this would take me or what I wanted to do, but I knew my sheer will and determination would provide a desirable outcome.?

Looking back, it was a whirlwind experience. Only one company called me for an interview—for an elusive Business Development Associate (BDA) role. I was completely unaware of what the position entailed, but despite that, I traveled to NYC and attended a full-day group interview with several elimination rounds. By the end of the afternoon, the hiring pool had dwindled from around twenty to three, and I was offered the job. Still clueless of what my day-to-day would become, I graciously accepted the offer.?

Eight years later, I’ve relished the glow of sales—huge logos, fat commission checks, and extravagant off-sites. However, like many, the industry has left me a bit bruised. The recent volatile environment has made selling software challenging, resulting in a contagion of RIFs that have impacted the most talented reps and have destroyed deals mid-cycle, depleting an entire quarter’s forecast. Frankly, it’s been difficult to predict where the market would lead.

But the rain clouds have been slowly lifting. I don’t know if this statement is cavalier, but I feel a Renaissance coming—a new age of selling software!?

Loading phone numbers into a dialer and blasting off email sequences no longer engages prospects and destroys your organization’s email deliverability rates. Even worse, interrogating discovery calls drives buyers to look at competitors with PLG sales motions. These techniques are antiquated, and buyers have become incredibly repulsed by them.?

Unfortunately, I don’t have the answer to what’s next. Still, for the love of sales, the craft, and the profession, I am committed to immersing myself in new ideas and methodologies and adding them to my repertoire of skills. Up first, Triangle Selling. But more on that next time.