Leadership Becoming: interruptions & deceptions

I truly love working with start-ups! I am totally in my “flow state” when building something new. ?? This is a story about an early seed-stage security vendor where I worked for just 60 days. ??♀?

How It Started:

During the interview process I had around 10 calls with the CEO and Leadership team over the course of three months, including several calls during my vacation. I took these vacation calls because I desperately wanted to escape a toxic environment at another vendor. My desire to just get out of a toxic culture at one company drove my delusional thinking in ultimately accepting an offer from another one. Lessons learned follow here…

Delusional Optimism: the Red Flags Ignored:

Despite noticing a whole lot of red flags, I ignored them. Vacation calls, after hour calls, group calls where the CEO is the only one talking…After one pre-hire call, I even texted two work friends saying it was a “fuck no” for me. The CEO seemed clueless about the Channel and was constantly interrupting discussions to assert his opinions. His opinion was the only one that mattered, and his opinion was treated as gospel by his team. They would simply stop talking and accept whatever this CEO said.

I kept talking to him and even created a 30-60-90 day Go-to-Market (GTM) plan at his request. My delusional thinking was that if he accepted my plan, then I would be able to affect change and help this company GTM with the MSSP Channel. Maybe I could have real impact here? I truly do love growing businesses and have a deep desire to make a positive impact wherever I go.

GTM Plan Accepted:

My GTM Plan was accepted and selected by the CEO and I received an offer of employment. I negotiated favorable terms and accepted the offer as this company’s first Vice President of Channel. The CEO hired a new CMO at the same time he hired me, the identity of which he had kept secret during my hiring process. This new CMO was also one of the worst experiences I’ve had with a “Queen Bee.” A Queen Bee is a woman who’s attained some level of professional success yet is fundamentally threatened by other women who may attain the same level of success. The Queen Bee will actively undermine another woman’s advancement.

Toxic Dynamics:

I despise workplace politics, especially horizontal hostility. During a one-on-one, I confronted the CMO about her behavior. She briefly revealed her insecurities, shedding crocodile tears about past experiences with mean girls. I told her that I too had similar experiences with nasty women and I had made a decision to never be like them. I told her that it was not the kind of person I am or wanted to be so I would never retaliate. And, I didn’t. Despite my commitment, she played a significant role in my departure.

Forging Ahead:

Even though there was so much dysfunction, I put 100% of my time and effort into executing on my GTM plan. There was constant friction with the new CMO as she wanted the GTM plan to be hers and hers alone. Also, I soon discovered the CEO had misrepresented revenue and partnerships. During the interview process, the CEO said they were trending toward their first $1M in ARR with over a dozen revenue producing channel partners. The truth was the company had one MSSP partner in South America who had made a single 5 figure transaction, and one in the U.S. for $450 MRR, far from the $1M ARR goal.

Tech and Market Fit:

The platform was intriguing but not a first mover. This platform targeted the SMB MSSP space due to strong competition in the Enterprise sector but received ongoing feedback regarding product/market fit and pricing.???????????????????????????

Was there even a product / market fit? The CEO claimed that since they were able to sell to his former employer, a big bank in LATAM almost 2 years prior that there was product / market fit. Silly CEO. A one-off transaction proves nothing other than you were able to leverage your relationship to get some money. We all can do that, but that doesn’t prove that there is really a product / market fit or even prove that there is a gap in the market that this product fills.

Challenges and Adjustments:

I adjusted my GTM Plan to address revenue shortfalls and product concerns. I clearly communicated to the Leadership team the challenges we faced in reaching our $1M ARR goal, and I made it clear how difficult this was going to be, how much effort was required, and what we needed to do from a product, partner program, and ecosystem perspective in order to set us up for success.

Positive Feedback and Sudden Change:

At this point it was too late to back out, so I continued working with the Leadership team and the few contractors that we had. The GTM plan was adjusted with the Leadership team’s heavy involvement and at about 6 weeks in, we presented the GTM plan to the investors. Green lights all the way through and consistent positive feedback from the Leadership team, investors, and the CEO. Note, the goals and KPIs were all identified and agreed upon at this time.

However, in week 7 the head of product announced the need for a complete platform rewrite (more deception), literally new code from the ground up. He believed we could continue to sell, and his team would support the existing platform, but all development efforts would focus on getting a new platform built asap. For channel this would delay ecosystem vendor integrations by at least six months, but more realistically a year.

Up to this point I was receiving consistent positive feedback from the CEO and the Leadership team members whom I had twice weekly one-on-ones with, along with our weekly sales and Leadership team meetings. We had a lot of meetings but there was a lot of activity, and we were a start-up so needed the proximity and communication.

In week 7 during our Leadership meeting, the CEO acknowledged that the product wasn’t ready and there needed to be a do over. We were told that the rewrite had already started, and we were moving forward with the GTM plan.

Consistent Prospect Feedback:

I had been having 2-3 calls a day with MSSPs in my network to get feedback on the platform. These were mostly demo’s with the head of product joining me on these calls to do the demos. One or two of these calls each week were with ecosystem vendors who might be a good fit for integration and co-marketing. During these calls, feedback was the same:

From MSSPs:

1. Great idea, needs more automation & integration.

2. I like the product but wish I had it before integrating my stack.

3. It’s too expensive.

From ecosystem vendors:

1. This platform fills a huge data gap for us.

2. We’d love to integrate and build a joint GTM plan.

3. Please share your API documentation.

CEO's Denial:

The feedback is exactly what I expected, and exactly what this CEO did not want to hear. He did not want to hear that there is a lot of potential, but the platform needs more work. He didn’t want to hear that there were huge opportunities in partnering with ecosystem vendors in this space who already had thousands of channel partners each. Integrations take time and the CEO wanted immediate revenue. Besides that, we were now rewriting the platform so no way to work on integrations.

At the end of week 8, exactly 60 days into the GTM plan that was approved by the founders and investors, the CEO told me that I was not making enough phone calls and I was fired. I challenged him on this and he admitted that there were enough phone calls, but he didn’t think I was talking to the right people.

Are you familiar with the phrase, “Don’t shoot the messenger?” The CEO shot the messenger, a classic mistake for a first-time CEO. The reality is that an unwavering belief in one’s product, devoid of humility or growth, leads to failure. End of story.

Toxic Behaviors

1. Micromanagement and Interruption: The CEO constantly interrupted calls to impose his opinions, disregarding the expertise of his team. This behavior stifles innovation and autonomy.

2. Deceptive Practices: The CEO misrepresented the company’s revenue and partner status during the hiring process. This dishonesty is a hallmark of toxic leadership.

3. Unrealistic Expectations: Despite clear feedback that the product needed more work, the CEO refused to acknowledge it and set arbitrary KPIs. This shows a lack of understanding and respect for the team’s efforts.

?Conclusion

It’s crucial to recognize these toxic behaviors early and decide whether the environment is right for you. Leaders who frequently interrupt and impose their views can create a stifling work environment. Setting unattainable goals without considering feedback is a significant red flag. And, misrepresentation of facts during hiring or project discussions is a true sign of toxic leadership.

Remember, you have significant value in what you bring to an organization. Don’t believe that you must accept abusive behavior just to get a paycheck. The emotional toll, the anxiety and the stress are simply not worth it. Advocate for yourself and seek healthier work environments where you can contribute effectively.

?I will share more of my toxic leader stories each week so look for this newsletter weekly. I’d love to hear about your toxic leader stories too! Reach out to me through the comments or DM me. I am building content now for a podcast on Leadership and would love for you to join me. #leadershipbecoming