How to land an interim leadership role… if you’re not Elena.

What to do, if you don’t happen to have $10B+ companies begging to work with you.

Hey, there!

I’ll get the bad news out of the way up front: This one is not from Elena. This is Jonathan Yagel. If you’ve seen my name, it’s probably at the bottom of Elena’s newsletters, because I help her edit them. Or maybe because of that one time I set a world record for the most high fives in one minute 🙌 😂.

No, yeah, probably just from Elena’s emails.

Anyway. The good news: I’m what you might call an Aspiring Elena. While she’s practically swatting away opportunities because of how popular she is, I’m… not. Yes, I’ve been a marketing and growth exec at B2B startups (not at decacorns like Elena has, though, come on) and have since left the world of full-time roles to focus on advising, consulting, and interim roles. I even have a (tiny) newsletter! But I don’t teach amazing Reforge courses or have a massive following or create the industry’s favorite memes. (… “yet!” I just said to myself, but even that feels a liiiittle cocky.)

Maybe you can relate?

So, Elena recently posted her excellent rundown on what Interim roles actually mean, but consider this an addendum. The reality is: There’s only one Elena. But if you (like me) are inspired by what she does, but aren’t on her level (yet?), I figured I could share my perspective on how I’ve landed interim positions and navigated independent work.

Here are 5 more tips on how to navigate this situation if you’re an Aspiring Elena, too:

1. General Advice: Make sure you’re prepared

2. Framework: Choose Your Route to Interim: Bottom-up vs. Top-down

3. Approach #1: Use Job Applications

4. Approach #2: Upsell from Contracting

5. Approach #3: Get Referrals

1. Make Sure You’re Prepared

Before you pitch yourself for Interim work, there are a couple key things you should consider:

Traditional Leadership, then Interim Leadership

Have you held an executive leadership role in the function you’re going for? This isn’t an absolute requirement, but generally, the bar is higher for interim roles. This is because:

(a) It’s often more difficult: You’ll have a shorter window and are still expected to deliver the same (or better) results; and

(b) Interim is not the norm: Because interim roles are still new for most organizations, you’ll have to overcome inertia—whether that’s explicit (colleagues complaining, HR opposing the necessary systems, etc), or implicit (colleagues just not knowing how to interact with you, HR just not having the systems in place yet, etc)

So, if you don’t have previous experience as (for example) a Head of Growth at the type of org you’re pitching, step carefully. If you’ve never been a Head of Growth at all, you may want to reconsider. This is important both because it will be hard for you to convince a company without relevant experience, but also because, even if you do convince them, you may be setting yourself up for failure. 

So, what do you do, if you’re looking to get out of full-time roles, but haven’t gotten to a senior enough position? There are several options, but the main thing I would recommend is to consider other non-full-time options, besides interim!

Interim vs. Fractional vs. Advising vs. Contracting vs. Consulting vs. Freelancing

Okay, wow, that sub-header got even longer than I was expecting. This could (should?) be a complete article all on its own, but to be prepared for these kinds of conversations, it’s worth clarifying these definitions. Elena pointed out the distinction between Interim and Full-Time / “Permanent” roles in her original post, but here are a few more important distinctions:

• Interim vs. Fractional: I think this concept was originally popularized by “Fractional CFO”s, because lots of companies need financial leadership, but can’t afford (or simply won’t prioritize) a full-time person in this function. Now, it’s bled into other functions (Fractional CMOs, CROs, CPOs, etc), but the general idea remains the same: A company is looking for senior executive guidance, but doesn’t have the need (or budget) to bring on someone full-time. So, this can be similar to an Interim role and the lines can get blurry here, but the difference is usually in the amount of hours worked per week. An interim leader is full-time (or pretty close to it), while a fractional leader is usually a day or two per week. But both are hands-on roles that involve both strategy and execution.

• Interim vs. Advisor: Full-disclosure: I often call myself an advisor and that’s been the description on some of my engagement contracts… and I give advice. So I’m an advisor, right? Personally, this feels a bit like when a PhD in Political Science says “Yes, I’m a doctor, how can I help?” Not teeechnically incorrect, but not what people usually mean. “Advisor” usually means you’re on an advisory board. But either way: Someone in an interim role is often indistinguishable from a member of the leadership team; an advisor is decidedly outside of the company, generally providing strategic guidance to the leadership team, with no responsibility for execution.

• Interim vs. Consultant: Consultants differ from Interim leaders in two particular ways: Although both provide strategic guidance, a consultant is generally around for an even shorter time and usually has limited accountability for the execution side of things. Consultants usually have even deeper expertise in a particular area, which allows them to come in, provide specific direction, and then move on.

• Interim vs. Freelancer: Most of us are familiar with freelancers—they’re sort of the opposite side of the coin from consultants. They also generally have a specific expertise and are contracted for a limited duration, but they are actually more similar to Interim roles, in that they focus on execution, as well as strategy. The point of contrast, though, is that interim positions are leadership roles, while freelancers are generally individual contributor roles.

• Interim vs. Contractor: “Contractor” is out of place with the rest of these, since it really just describes the nature of the relationship between the organization and the individual. The term is often used as a synonym for freelancers, but consultants, fractional leaders, and even some advisors are paid through a 1099 “Independent Contractor” form. Here’s how the IRS defines it, if you’re curious. As Elena pointed out in the original article: Some interim roles are paid through 1099 forms, and some are paid through W-2 forms (as a regular employee). Which is all to say: “Contractor” is kind of a catch-all for all kinds of independent, non-“permanent” roles, so it’s not as much of a useful distinction.

Now, back to Interim: you can see the contrast between the concepts mentioned above and Elena’s original definition:

“An interim leader is a short-term (~1 year), full-time, contract-based leadership role that steps in for a limited time to steer a company through a transition, cover for an absence, or lead a specific project. Unlike full-time leaders, who are expected to stay for many many years and constantly evolve their contribution as the business grows, interim leaders are there for a specific purpose and predetermined time. They bring expertise and an outside perspective, often driving change or stability during critical periods.”

So, what’s the point of laying all of that out? The point is this: Just because you’re not happy with traditional, “permanent,” full-time roles doesn’t mean Interim roles are your only option. 

In fact: If you’re an Aspiring Elena like me, some of these other roles may be a necessary bridge to getting into Interim work.

SIDE NOTE: In my experience, there’s a lot of “positioning” around these terms, because there seems to be a kind of hierarchy of status around the terms: Freelancer / Contractor < Consultant < Interim / Fractional < Advisor.

That’s probably because this progression reflects increasing degrees of seniority (and compensation). So, I don’t necessarily knock that guy who was a “Web Design Freelancer” last month and is calling himself a “Fractional Chief Design Officer” this month—maybe that’s a path to getting some much-deserved recognition. But I’d recommend figuring out what type of role you want and have the experience for, and owning it. Just like full-time employees progress in their capabilities, independent workers & solopreneuers can, too.

2. Choose Your Route to Interim

What originally prompted me to write this post was reading Elena’s article, where she shares in specific detail how she landed her interim roles. These stories were both deeply interesting and completely foreign to my experience: 

“​​Netlify … had a laser focus on me…” 

“Amplitude’s CPO reached out to me…”

“Dropbox reached out…”

What this revealed to me is that there are two different paths to Interim roles:

• Top-Down (aka Inbound): This is what Elena was describing, above. She’d already developed a reputation as an advisor and generally operates at the board level for these companies. For her, taking interim positions was a natural extension of a successful independent career.

• Bottom-Up (aka Outbound): For me, the approach has to be reversed. While I’ve still ended up in Interim roles, the process has started on the other end of the spectrum: Focusing on consulting or even execution-focused contracting work.

So, the first step is to determine which path you’re on—and if you’re not already on a board (or several) and being pursued by the C-suite of companies worth 11-figures, you may need to take the bottom-up route, too.

3. The Long Shot: Use Job Applications

What’s the easiest way to figure out if a company needs someone with your specific skills? A big ol’ public job listing with your ideal title sure is a good start. 

This is how I landed my first interim role, with Simon Sinek and The Optimism Company. 

I’ve been a fan of Simon’s work for a long time, so I was excited to see that his company was looking for a Head of Growth to help them launch and develop their learning & development platform. As I went through the application process, the leadership team and I realized that an interim arrangement would be better aligned with their objectives. They got rapid impact from me during a moment of substantial transition, and I was able to work with one of my role models, without completely detouring away from product-focused technology startups, where I’d spent (and am continuing to spend) my career.

Takeaways:

1. This is probably the most cumbersome approach, since job applications can be miserable, but it’s often the clearest way to confirm that a company has a need for your skillset. 

2. Interim roles can be a great opportunity to work with people or companies you admire, without totally derailing the focus of your career.

3. If you’re interested in an interim structure, remember that this arrangement can often be super beneficial to the company, too. 

4. The Long Haul: Upsell from Contracting

Back to the point about choosing your route: Starting from a more limited engagement is probably the most likely path to success. Job applications are rough and pivoting a role to interim isn’t guaranteed—but most companies need help from high-quality talent. 

This is how I landed a role with KleerCard, a fintech startup that does corporate cards for non-profits and SMBs. I initially worked with them for a very specific engagement: To clarify their positioning across multiple audiences and several products. Throughout that process, we enjoyed working together and when they indicated that they needed broader marketing leadership, I pitched an interim/fractional CMO role, which they agreed to.

Takeaways:

1. Identify specific areas where you can provide significant short-term value.

2. Be patient. Contracting and consulting may not come with the same degree of clout as Interim roles, but if you’re just getting started, it’s a great way to hone your skills across a variety of companies. If you’re new to this style of working, in general, I’d recommend checking out Tom Critchlow’s Map for Indie Living.

3. Develop a bias toward impact & accountability. A clear-cut set of deliverables provides an impressive degree of focus. If you’re mostly used to full-time work, then having a very specific deliverable and a limited timeline may be a valuable learning experience. 

4. Bonus: While a true interim role generally means a full-time (or almost full-time) commitment, contract work can be done as a side hustle. Again: If you’re in a full-time role and looking to start down a different path, this kind of contract-based work can bring extra income, extra experience, and the relationships that will make it easier to jump into a full-on interim role.

5. The Long Game: Get Referrals

This one is actually the most similar to Elena’s “inbound” approach, and has a bit of a Catch-22 element to it, but using your network is generally the best way to consistently get Interim positions. 

This is how I landed my current interim position with VIATechnik, one of the top firms in construction technology. They’ve had incredible success as a strategic partner for some of the largest construction projects of the last decade, and are a powerhouse in their industry. But now they’re looking to accelerate their growth and draw more attention to some of their new products.

I was introduced to their team by a former client of mine, and am helping them develop a more robust marketing function—which gives me ongoing flexibility, while giving them the opportunity to understand the growth model that makes sense for them, and how to hire for it.

This kind of intro is the ideal end goal for getting this type of work—you’ve built a viral engine where each new engagement leads to more engagements for you! But, fortunately, you don’t need to have existing clients to make this approach work for you. Regardless of the depth of your network, everyone has colleagues and former employers. Just let people know that you’re open to this kind of work! If you’ve done good work in the past, you may be surprised at what comes your way.

Conclusion

So, there you have it. Once you’ve thoroughly prepared and chosen your general route, you’ve got 3 different approaches to landing interim roles: (1) Job Applications, (2) Upselling from Contracting Work, and (3) Getting Referrals.

As one final note on those approaches: It generally won’t be as clear cut as those specific paths! In fact, each one of the examples I mentioned actually included two out of three: A friend referred me to the recruiting team at Simon Sinek Inc, before I went through the job application process (#1 + #3); I knew KleerCard’s CEO before we did the original contracting engagement (#2 + #3); and I also did a limited-scope engagement with VIATechnik, in addition to getting the referral (#2 + #3). All of that to say: There’s no single route, but I hope these elements help you on your path to an Interim role… even if you don’t wake up every morning with an inbox full of fanmail (I don’t know if Elena does this, I’m just assuming).

All joking aside, though: when my last startup died almost 2 years ago and I was trying to decide what to do… Elena’s posts helped me realize that an alternative path was possible, besides raising more money and starting over again, or just getting a more traditional 9-to-5. A lot of it has been rough and very stressful. But at this point, I’m making 5x what I made in my last full-time role (which actually says more about how little founders pay themselves than how much I’m currently ballin’, but that’s another post) and I’m feeling confident that this independent thing can work for me.

If you’re an Aspiring Elena, too, I’d love to connect! You can drop me a line on Linkedin or subscribe to my aforementioned tiny newsletter: 1, by Jonathan Yagel.

Thanks for reading!

Jonathan

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