Broken Rollercoaster

Leslie Venetz shares her rollercoaster journey in sales from making 150 cold calls to founding her own business...

April 10, 2022

My Rollercoaster Ride in Sales

By: Leslie Venetz

Naivete was my superpower in my early 20s

If I had known how hard it would be to move from Montana to Chicago and then survive on a salary of $18,000, I would have said, “no, thank you.” If I had known how exhausting it is to make 150 cold calls to Fortune 500 C-suite execs every day, I would have taken a hard pass on a job in sales. If I had known the Great Recession was only a few months away, I would have talked myself out of beginning a career in B2B sales.

That naivete was a blessing, but it was also a curse. I didn’t know any other women in B2B sales. Heck, I didn’t know anybody who had “made it in the big city.” Without a reference point, I assumed that struggling to make ends meet, sexual harassment, bro culture, and a toxic workplace was the norm. I thought most women went home at night and cried.

Riding a wooden rollercoaster

My sales career has been like riding a wooden rollercoaster that missed its last few maintenance checks with exhilarating ups, terrifying plummets, and a worry that it might launch off the track at any moment.

It took a decade for me to realize that I wasn’t alone and that it shouldn’t have to be this way for women in sales.

In 2018, I founded Sales Team Builder as a purpose project. I had just launched and successfully scaled a successful minimum viable product as employee number one at a startup. If I could do this for somebody else, I figured I could do it myself. I knew women deserved better, and I wanted to help (but I didn’t know how).

I spent two years connecting with others, creating content, and sharing my story. I wanted to inspire women to explore a career in sales and make it safer for them when they get here. I was proud of my work but still didn’t view it as a full-time job. I was scared to leave the perceived comforts that corporate America provides.

Then 2021 broke me

From the outside, it looked like a banner year for me. I released a well-received playbook, my TikTok was taking off, Sales Team Builder was thriving, and I was smashing targets at my day job. Nobody saw that for most of 2021. I was unhappy and conflicted.

I was languishing in my job, but it felt irresponsible to leave. I interviewed for new roles, but the sexism and total lack of respect for the profession of sales were overwhelming. I felt stuck where I was but wasn’t sure what came next. I stopped interviewing and started giving voice to the possibility that I could focus 100% of my time on Sales Team Builder. It felt scary, but it felt right.

Turning down my dream job

Then I got my dream job offer. It was what I’d been chasing all year. It was the perfect step on the path to CRO I’d been working toward for 15 years. It’s what I thought I wanted. I turned it down. At that moment, I realized that my work with Sales Team Builder was my calling. I started Sales Team Builder because women deserve better.

And I want to help.

The Weekly Pitch: How is Sales Team Builder different from the oft-male dominated sales consultancies?

Leslie: Just like there is no one way to sell, there isn’t going to be a sales consultancy that is right for everybody. My challenge is this: start by recognizing that almost all historical thinking about B2B sales has been created by white men for white men. Ask yourself, "what am I doing to incorporate historically marginalized voices into our sales processes, scripts, techniques, and sales culture?"

I understand that not everybody is ready for my message of inclusion, sales as a respected profession, and putting your buyer at the center of everything you do. I believe the sales world is evolving, and I’m here to help the organizations that are ready to level up to meet the needs of the modern B2B buyer.

The Weekly Pitch: What is Sales Team Builder's go-to service?

Leslie: I support early-stage Founders and small business owners who are 6-12 months out from hiring a full-time VP of Sales but need strategic sales support now. I take work off of a Founder’s plate at a critical time for the business and give the commercial team extra attention so they can uncover more wins. I create repeatable processes and playbooks.

I also support sales leaders with training engagements. I run an interactive coaching workshop series that gets rave reviews. After creating a custom syllabus for the training that could include anything from active listening to the anatomy of a cold email, I run virtual small group sessions where we create deliverables that sales teams love to use.

The Weekly Pitch: Why aren't more women in sales leadership positions?

Leslie: More women aren’t in sales leadership because of gender discrimination. A combination of outright sexism, unconscious bias, “bro cultures” that keep women from feeling safe, or even cultural attitudes about what jobs are appropriate for women, prevent us from considering careers in sales.

We are closing the gender gap in sales, with women representing about 35% of B2B sales professionals. However, women fill only about 15% of B2B sales leadership roles.

Even though women are often paid less and have to constantly manage the mental burden of toxic sales cultures and sexual harassment at more than double the rates of men, they still tend to outperform men.

The reason that more women aren’t in sales leadership is that they aren’t given a chance.

The Weekly Pitch: How can we give women more chances?

Leslie: Every organization and sales leader needs to be intentional about amplifying women's voices. This goes beyond diversity. It’s not enough to hire women if you aren’t investing in them and creating a space where they feel safe. It’s not enough to invite women to the table if you aren’t listening to them. If you aren’t taking action to fix the problem, you are part of the problem. I don’t have all of the answers, but I believe it goes beyond conversations about diversity to understand what inclusion and equity mean for the sales profession.

The Weekly Pitch: What's a must-add tool to the sales leader's tech stack?

Leslie: This is a tricky question because I am obsessed with tools like Lavender, iorad, and Tolstoy. But if it’s a “must-add,” I think there is a chicken and egg tie between a data enrichment tool and a Sales Enablement Platform [SEP]. It doesn’t matter how great your processes and sequences are if you don’t have clean data, but it doesn’t matter how great your data is if you haven't created buyer-centric sequences. Automate as much as possible so your rep's time can be spent on selling, not admin.

The Weekly Pitch: What are the top sales metrics leaders should track?

Leslie: I get a bit sensitive about vanity metrics like bragging about open rates when the reply rate to your sale call-to-action is zero. But a trick many sales leaders miss is that metrics don’t matter if the inputs aren’t accurate. Leading organizations are automating many of these inputs, which increases consistency and frees up time that would otherwise be spent on admin.

Assuming you don’t work for an organization with a next-level tech stack and fully automated deal process, I’ll exercise restraint and suggest only five metrics.

  1. Number of discovery meetings (assuming disco and demo are both done on call one).
  2. Number of discovery meetings that do *not* progress to the next step and the reason.
  3. Number of opportunities created.
  4. Average sales cycle.
  5. Average deal size.

The second metric might throw folks for a loop, but I’ve found that most leaders wait to coach at the end of the process, or they coach deals instead of coaching people. If you watch what happens after the first meeting, so many great coaching opportunities will present themselves. Are they not meeting with the right people? Are they struggling to overcome objections? Do they need training on needs analysis? Why wait to do a retro when a deal is closed/lost when you can start that conversation earlier?


The Weekly Pitch: If sales leaders need your help, what's the best way for them to contact you?

Leslie: Anyone can learn more about Sales Team Builder here. You can also connect with me on TikTok at SalesTipsTok or on LinkedIn.

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