The Real Reason Women Aren’t Getting Ahead in Tech: “She’s Not Strategic”

Jess Iandiorio
The Startup
Published in
9 min readAug 22, 2020
Pro tip: Learn to own the mic. Extra points for jazz hands

Before I explain “She’s not strategic,” I’d like to give you a bit of background. I’m 38 years old and a two-time CMO for tech companies. I’ve joined five startups so far and held leadership positions at four of them. Along the way, I’ve had three children, and in my child-bearing years advocated for how to make tech family-friendly, how to handle exec pregnancies with “Oh sh*t! Your top female talent is pregnant, and my perspective on how to address the leadership gap: The Women In Tech Convo Needs More Men.

As my hair stylist starts to address the beginning of gray hair by saying, “Seriously, it’s not noticeable,” and my sister says, “HA! You’re going gray!” I find myself entering a new era of gray hair + perspective. That same gray hair I felt the lack of for all those years. Now I’m in da club, and my perspective has changed.

I used to see maternity leave time-outs — and the subsequent feeling you can’t ask for a raise or promotion — as one of the core issues creating the wage and leadership gap. Now that I’m on the other side, I’ve noticed a very different issue. I call it: She’s not Strategic (SNS). In this article, I want to explain what I mean, how women can spot if they’re suffering from SNS disease, and how leaders (men and women) can recognize if they’re not giving promising women a fair chance.

What do I mean by strategic?

Leaders are chosen for their ability to impact the trajectory of the business over time. Being strategic means you’re able to balance long-term objective setting alongside near-term actions and goal setting. It means you understand the market you operate in, the ancillary markets, and all of the factors that will contribute to your organization’s success. While you typically only lead one function, you actively contribute ideas everywhere. Your strategic impact is not based on individual/functional performance, but how you contribute to the success of other functions.

What’s “She’s not Strategic?”

This a bias-based issue. Both women and men in leadership are prone to unfairly judging a woman’s potential to have a broader impact. This great HBR article points out that in addition to individual biases, organizations are often prone to structural biases that prevent women from getting ahead.

I’ve seen it happen at least a dozen times to women who can’t seem to break through the Director or Senior Director level to VP+. While the surrounding circumstances are unique, the context is the same: A talented woman is asking for a promotion. This woman is typically highly valued and well known for her operational excellence. Everyone agrees she “gets sh*t done.” In many cases, she gets more sh*t done than anyone else. But when the decision comes on whether she’s a fit for the VP role or not, the whispers start, “But, she’s not strategic.” And the woman gets passed over.

Because this woman never gets the promotion at her current role, she carries the stigma when she becomes disenfranchised and applies to another company. The new company notices she never was promoted to a leader and she gets a lateral offer. “We’ll put you on a leadership path,” they say.

I’m preparing to be criticized for this, but I’d bet at a minimum 50% of the times that a woman is labeled “She’s not strategic,” it wasn’t the case. The reality is that she was so excellent at executing, she was given more and more work, and she executed. She did not have the space and time to become more strategic. Could she have made time in her night-time hours to reflect and bring a new idea to the table? Maybe, and maybe not. Often organizations take their top performers and legitimately overwhelm them with work, and there simply isn’t time to step back. There’s only time to execute.

The rub: Not everyone is meant to be strategic

Sometimes she’s not strategic, and sometimes he’s not strategic. Some people are built to operate and execute someone else’s playbook flawlessly. They bring passion and drive to their pursuit of exceeding goals set by others. And that’s their lane.

But it’s just as often not the case. My purpose in writing this article is to encourage others to check themselves before they write someone off as not strategic, especially if they’ve been a top performer. It negatively impacts you to lose them, and you stand a lot to gain through retaining and growing top talent.

How do you spot SNS in the wild?

I’d love to hear other perspectives on this. If you hear yourself say “She’s not strategic” (I have said it myself), consider these three questions:

  1. Has she been able to recruit & retain a high-performance team? There’s a lot to be said of someone who can sell the company and successfully recruit strong performers. This requires inspiring people with strong verbal communication and an ability to share the company’s vision and goals. People don’t go work for managers who don’t inspire them. So if she’s been able to do this, there’s strong potential. If she’s not had a team, or a chance to build a team, give her the opportunity first to suss the potential out.
  2. Has she brought new ideas to the table that had a positive impact on the business? Leaders don’t see problems and complain. Leaders come up with solutions and make sure those solutions are heard. If this person saw a problem and suggested a solution that was good enough to be implemented, and made a positive change — think again about her potential. If it’s not obvious who made the contribution, ask her. Maybe she did come up with something but the manager above her took credit. If she can’t come up with anything, you should make it clear what’s expected of leaders.
  3. Does she understand all functions in the business? When you think about the lifecycle of the customer, does she understand the interconnectedness of all the functions that attract, sell, serve, and retain customers? While executing, women (and men) can become so tunnel-visioned on their function that they don’t pick their heads up and think about how it affects other functions. Sometimes this can result in short-sighted behavior. An example would be if a woman has a lead goal, celebrates hitting it, but unfortunately, the sales team missed their number. This shows short-sightedness and a lack of organizational awareness. Success is about the entire company, particularly at a startup.

There’s my guide: If a woman can recruit & retain a high performing team, has contributed solutions to problems beyond her charter, and understands the dependencies between all organizational functions — she’s strategic. Now give her the space and opportunity to do more.

To all my ladies: What do you do if you’re suffering from SNS?

If you’re confident you deserve a promotion and believe you’ll be passed over, here’s my advice:

  1. Make sure your strategic contributions are clear. If you created a solution to a problem, and no one knows it’s your solution, that’s your new problem to solve. Your contribution needs to be clear or else it doesn’t exist — that’s a hard truth.
  2. Contribute to the overall health of the business. Executives are focused on building the business — they care about people strategy, growth strategy, retention strategy, and financial health. If you’re not contributing ideas on all fronts, start now. Your function doesn’t matter — you can impact everything. You can suggest a new recruitment strategy, try to bring in leads from your network, contribute to customer success, and find ways to make or save the company money.
  3. Up-level your presentations. In forums where you’re presenting, always take a step back and set the context. Don’t dive into details and numbers right away. The level of detail you operate in can’t be easily understood by execs. Always open with, “Before we get into the details, just a quick reminder — here’s our strategy. Related to how we’re executing on this strategy we have three key takeaways for you.” While you may think this removes the opportunity for you to share the great details of your work, it’s actually giving you a better platform to showcase your strategic impact. Execs will walk away thinking you can articulate what’s working/not in your function.
  4. Understand the difference between management and leadership. Proving yourself as a manager is critical to becoming a leader. But being a good manager doesn’t make you a strong leader. We’ve all had difficult team members that are tough to motivate and manage; At worst they seek to undermine you and at best they constantly challenge you. Leaders are able to take these employees and either remove them, or inspire them to do their best work. Leaders are people that team members want to work hard for, not against.
  5. Build your visibility — up. Here’s an important distinction: I didn’t say build up your visibility. You need to focus on building your visibility upwards. If you want to move up, you need champions who are higher up than you. This is your boss, alongside their peers, all the way to the CEO. There are a lot of ways to do this.
  6. Always participate in company-sponsored activities. Execs will be there, and in the world of digital-burn-out, you’ll have an opportunity to stand out. You’ll at least make a positive impression for being committed and being a leader. If this makes you feel extra-taxed because you already have family commitments — I hear you. Do as much as you can.
  7. Spot problems, suggest solutions and make sure people above you know you’ve suggested solutions.
  8. Ask smart questions in front of large audiences. There’s no better way to be seen and heard by execs than being the only person that speaks up in a company meeting. Come up with a question about your market, competition, or growth strategy and you’ll be noticed for intelligence and willingness to speak up.

These are all good ways to increase your visibility and make positive impressions so that execs will remember you’ve spoken up, participated, and contributed.

But how do I do this remotely? Especially now!

As we all know, 2020 is a complete nightmare, and 2021 is looking like the sequel. So let’s try to silver-lining the sh*t out of this. Maybe the pandemic and remote work could be viewed as an opportunity.

A recent HBR article asked, “Will the Pandemic Reshape Notions of Female Leadership?” In the article, there are shining examples of the leadership and success of female-led countries throughout the pandemic to date. It states, “The roller-coaster ride of gender equality over the past few decades may be depressing to some. But this moment, unlike any we’ve ever known, opens new options for the future — millions of them, in fact. This group of talented leaders may become the first visible wave of role models for the generations to come, redefining the way we pick leaders in politics and business.”

And there’s Kamala 🙌 Now, “more than ever” female leaders are on the main (virtual) stage.

Here’s advice for how to stand out when no one’s meeting face-to-face::

  • Create your shining moments. No one is going to create moments for your ideas to shine, so you’re going to have to do it. Set up a meeting to discuss a problem/solution regarding something execs care about. Bring your ideas to the table. If there’s an existing meeting you’re not in, ask to join it. Or find an interesting way to share your idea asynchronously.
  • Pre-sell your ideas before the meeting. Take the time to pre-pitch your idea on a 1:1 basis with a key stakeholder. This will give them an opportunity to shape it with you, and when you’re ready for prime time, you’ll have champions.
  • Bring it on zoom. People are stressed/overwhelmed/anxious… and it’s visible. Not you. You’ve got your sh*t together. Maybe you even put a casual blazer on. Professionalism isn’t canceled — show people you’re a boss.
“It’s business time” — Flight of the Conchords
  • Stay positive and focused. Everyone has their stories and challenges relative to COVID — you do too — but focus on work. We all have a limit to the emotional energy we have on any given day. The more you talk about COVID, the less energy you have for work, and you’re missing opportunities to contribute & shine. Give it limited space, and be the person in the meeting that says, “Enough about that mess, let’s get to work.”

I’ve navigated being one of the only women in the room throughout a 16+ year career in tech. 16 years later… not much has changed. There’s so much subtlety and bias preventing qualified women from moving up; I hope this helps people consider their actions and if the SNS diagnosis is fair or not.

I’d like to thank Niall Fitzpatrick, Colleen Tartow, Erica Orthmann, Mandy Darnell, and Justin Borgman for their feedback and support.

Check out www.starburstdata.com to learn more about what we’re up to & see our open roles!

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Jess Iandiorio
The Startup

CMO @Starburst, former CMO Mirakl, VP, Mktg @Drift & VP, Product Mktg @Acquia. Love start-up culture and being SaaSy. Also love being a mom & wifey.