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Summer Poletti

Maximizing Your Return: Strategies for Getting the Most out of Fractional Sales Leadership Engagement


Welcome back to our Fractional Leadership series, if you missed the last post on the fundamentals, check it out here.


We previously highlighted that fractional leaders bring a wealth of experience and expertise without the hefty price tag, overhead costs and perks packages of full-time executives.


Even with that understanding, one of the most common hesitations I hear is "how will I get my money's worth?".


I'm not telling you anything you don't know, but to ensure a successful project with a fractional leader, it starts first with the CEO or owner. You. So here are some things you can do to help ensure success.


Be very specific about your objectives


Ideally before you start talking to fractional leaders, but definitely before the project launches, it's a best practice to get very specific about what you expect to get out of the engagement. If you're new to the concept of fractional leadership and could benefit from speaking to a few fractionals or maybe one that you trust, I'll give you a pass. Go ahead and learn about what they can do and what you can expect to expect. But before they start, figure out what success looks like to you. Otherwise they're driving the boat.


  • Clearly define what you want to accomplish with this fractional leader.

  • Articulate your vision for what your company should look like at the end of the assignment.

  • Estimate the duration of the engagement.

    • Are you looking for someone part-time on a permanent-ish basis until you grow large enough to need a full-time executive?

    • Are you looking for an interim leader who can fill an open role while you're sourcing new talent?

    • Are you looking for someone to help you solve a challenge?

    • Be prepared to negotiate on the timeline. In my experience, owners often underestimate how long a project will take.

  • Set 1-3 key SMART goals (Specific, Measurable, Achievable, Relevant, Time-bound), including clear metrics and timelines.

Side story: I once refused an assignment at a time when some extra money would have been nice. The company was transitioning from founder-led sales that were mostly to people within the founder's network or referred form investors and board members. Even then, a 6 months+ sales cycle, not uncommon in the SaaS world. Virtually no marketing and not much of a database of leads that hadn't already been sold. So we're talking cold outreaches. Startup mode, I get it. But here's the kicker - they wanted to know how much I would sell in the first 30 days. Reasonable and achievable goals, folks.

Establish a clear reporting structure


You can do this during the launch or very shortly after the launch, as this will require alignment with your fractional leader. You can know in advance who you want them to report to, often it's you. If your company is larger and more complex, you might have them reporting to a COO, CRO, etc.


Also understand if you want your fractional leader to manage an existing team. This is often the case with a fractional leader, but not 100%.


Lastly, during the kickoff with your fractional leader, establish regular reporting or check-ins, like you would with a standard member of your team. I like weekly for most fractional engagements unless they 10 hours or less per month. Daily is overkill, you don't hire a fractional executive to micromanage them, But when you're likely paying a monthly retainer, a monthly check-in is insufficient.


Another side story. This is a lesson I learned the hard way. I was working with a CEO to transition away from owner-led sales and hire, coach and manage their first salesperson. I was taking a while to find decent candidates (isn't that always the case?). There was a lot of foundational work to be done: sales strategy, lead generation strategy, strategic partner program, sales training program, sales playbook. Often the case when an owner has led sales. So I buckled down an wrote strategy and sales playbook, very labor intensive. But without frequent check-ins with the owner, he wasn't aware. Come end of the month when the invoice showed up, he thought I hadn't done any work since we didn't make a sales hire. We got over it - he eventually got his completed sales playbook and I got paid. But it was awkward for a bit. Get aligned on regular reporting.

Manage expectations with your team


I saved the hardest for last. Be very clear with the other members on your team that you expect them to collaborate with the fractional leader just as they would with another executive in your company. Also be very clear with anyone who will report to the fractional leader – they need to understand that this person has the same powers and responsibilities as a leader within in the company and that you expect them to receive the same cooperation. This is especially important if you’re bringing in the fractional leader to course correct an underperforming team.


Side story. This time it's one of my partners, another fractional sales leader. He got brought in to address revenue stagnation, something the CEO thought was because the salespeople were lazy or weren't working hard enough. Turns out the problem was actually the sales manager had a problem being a buddy and not holding people accountable. A common challenge. So with a buddy manager and team who had gotten used to loosey-goosey working conditions, the fractional VP of sales had their work cut out for them. Unbeknownst to him, this company had a habit of bringing in coaches, consultants and sales trainers, so the team was ready. They ignored and complained, and 90 days in there were no results, and the fractional contract was cancelled. Team still underperforming, but now with several thousand dollars wasted.

Recap:

There is more to it, but these are the big ones:

  1. Set goals before you start a fractional engagement so you know what you're investing in.

  2. Establish reporting structure and reposting cadence with your fractional leader.

  3. Manage expectations with your team.


Do you have experience with or as a fractional leader? Leave a success secrets in the comments.


Ask Yourself:

  • "Have you ever faced a challenge in your business that could have been navigated more smoothly with experienced leadership?"

  • "What areas of your business could benefit most from the expertise of a fractional leader?"

  • "Can you imagine overcoming a major business hurdle with the help of a seasoned expert, without the long-term commitment?"


Call to Action

Stay tuned for more insights on fractional leadership. Subscribe now so you don’t miss our next post, which will be a deep dive on the myriad benefits of engaging fractional leaders. If you have any questions or related stories, I'd love to hear them. Share your thoughts in the comments below or reach out directly! theriseofus.success@gmail.com


Rise of Us is a practice run by Summer Poletti, specializing in revenue growth: sales, strategic partnerships, customer success, marketing alignment. We generally work with financial services and SaaS companies from $2MM - $20MM ARR and help them plan and execute for their next stage of revenue growth. We concentrate on strategy, coaching, and organizational alignment.

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