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My First Toxic Startup Experience Wasn't My Last

Written By: Jessica Benjamin

I've spent the bulk of my career in media sales. From alternative newsweeklies to job boards to SaaS products, I like using a network of media to help clients reach their goals.

Some sales jobs are fantastic. You learn new things and genuinely help your clients solve problems. You can make friends with people who can change your career trajectory, help you get promoted, and stay there for years.

Some are full of surprises, but not the good kind.

According to HubSpot, the average sales rep tenure is 18 months. This is troubling. Xactly Insights data shows that sales reps hit their peak performance between two and three years in their role. That means most reps are leaving before they've reached their maximum potential. Why does this happen? Are companies providing enough training and ramp to their new hires?

In looking at this data point, I gained a better understanding of why some of my jobs didn’t work out. Whether you've had several short stints on your resume or are in charge of hiring, this is good to take into consideration.

In 2001, a recruiter at a newspaper ad placement agency contacted me about being the director of a new project that would be a page or two of national classified ads placed into daily papers, adding up to 4 million in circulation. The main competition was USA Today. I hesitated about the market fit, but the office looked cool, and when I pushed back, the founder offered me double the original salary.

This was my first VC-based startup and the venture capital employees sat right in the office with us. I was provided with a call center and hired two salespeople. There were a couple of problems. I was the only one who could sell the ads. These were often ads in categories the daily papers didn't want anyway, light scams like fortune telling 900 numbers, Multi-level Marketing, Mystery Shopping, and so on.

By then, I was meeting with the founder at a diner down the street and realized he was no longer welcome in the office.

Six months later, the axe fell without warning. The CEO walked past me in an open hallway and told me the national classified pages project was terminated. They didn't have an open territory for me to sell their main product, ad placement. I was the person who had to break the news to the founder about his project.

I was put on hold and told to try to sell a block of franchise ads, something I had zero interest in doing. I tried negotiating to sell a different category, but there was no leeway. Massive layoffs swept through the company, including the lovely woman who recruited me in the first place.

I was asked to write a postmortem and finally saw the business plan. I dug into it and realized it was primarily based on some calls with advertisers who said they would be interested in the model if it existed. There's a big difference between being theoretically interested and actually buying something. People have an ingrained tendency to say they are affirmative and then later prove less interested.

Also, the founder met with people at a news media association who were getting paid to run public notices, for example, legal notices. I knew getting national legal notices would only be possible if we disclosed our network of newspapers before publication, which would kill the business model.

A high-level operations person approached me and told me that if I could hang on for a bit, there would be "big changes." Instead, I started my first business, took the LSAT, and applied to law schools before the CEO and my manager, the VP of Sales, were let go.

Throughout my career, I've had several short-term stints. These are red flags that bothered me and might be helpful to note if you have experienced similar cultural elements:

  • A charismatic serial entrepreneur founder

  • When women were in positions of authority, it was usually in HR or Marketing.

  • Reporting to a thirty-year-old white male manager who was not responsible for recruiting, retention, or training.

  • Recruiters handled recruiting, learning, and development departments dealt with training, and some managers stopped taking responsibility for those functions.

  • The demand for Enterprise Account Executives soared in 2020 when people realized they could do these jobs more efficiently from home, then crashed with the economy.

  • Everyone knows someone who was laid off or fired over Zoom.

So, how do you avoid these short-term stints that can wreak havoc on your bank account and mental health?

Ensure you understand the business model, key performance objectives (KPIs), your compensation including stock options, and your hiring agreement. Things like non-competes and NDAs for salespeople should cause you to pause before signing. Have an employment lawyer review your agreement and anything you need help understanding.

Ask to talk to one of your future peers and your future manager before accepting an offer. I once had a job described to me as "a lot." I assumed they meant intellectually challenging or a lot of software to learn. It meant twelve-hour Zoom workdays, work on the last weekend of the month, highly restricted PTO, trying to placate clients who had yet to read their contracts, and a manager who didn't want me on his team.

I have no issue about working over the weekend and have many times, but I like to have the authority to decide what's worth my time if I'm working 60+ hours a week.

I have a long list of questions I ask before accepting a job. I've added asking if I can take two one-and-a-half-hour slots of physical therapy during the week. Suppose someone doesn't allow that small amount of flexibility or is uncomfortable that I need physical therapy after years of sales and millions of dollars sold. In that case, I know it won't be a love connection.

Every bad fit I’ve had with a sales job has been due to insufficient discovery during the interview process. There would be more good matches if interviewing were less like dating with more truth-telling about the job and company culture. I recommend more transparency during the hiring process. Applicants can seek out information from past employees on sites like LinkedIn. Companies should openly provide applicants with opportunities to meet with current employees who would become their peers. Such exchanges can help both employees and employers avoid working relationships they don’t enjoy.


Meet the Author

Jessica L. Benjamin

Jessica L. Benjamin, JD, is a people connector who does sales, fractional sales management, recruiting, and content creation. She can be found working for clients in her local community and around the globe. She likes dogs and big plants.


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