Alright – so today we’ve got the honor of introducing you to Hilary Swan. We think you’ll enjoy our conversation, we’ve shared it below.

Hilary, thanks for joining us, excited to have you contributing your stories and insights. To kick things off, we’d love to hear about things you or your brand do that diverge from the industry standard.

Sales makes so many people cringe, and it holds a stigma. This is especially true for sales leaders. A sales leader or head of sales, regardless of talent, tends to be one of the highest-paid people in the organization and startups and small businesses are often guided to make this hire early on. The head of sales is sales rep #1 and where this can become a high issue is when the role shifts into a true leadership role. Incredible reps don’t necessarily make incredible sales leaders.

Someone in my network reached out after acquiring a small business and the head of sales left on day 4. The CEO would have exited him in time, but the timing wasn’t ideal. This led me to a deep dive into the head of sales roles in startups and small businesses. The churn is high, the talent pool is grim, and the success of the business is dependent on sales. This is a recipe for a lot to possibly go wrong.

The fractional model is taking momentum, but can this be successful in sales leadership? 1000x, YES! Having access to a sales leader, on a fractional model, has proven to be wildly successful.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I got my start out of college with an inside sales opportunity in Los Angeles. I packed my bags and piled into an apartment with a co-worker. From there I went on to sell, disposables, commodities, medical devices, capital equipment and Saas. Sales was hard but very rewarding but it was time for the next challenge. Sales leadership!

Next thing you know I am running a sales team across 3 different divisions. The team grew from good to awesome. They were hard-driving reps in their own bag but we created a culture to cross-sell and invite each other to meetings. They created opportunities for each other and while not one of the reps was required to do this, it made it better. The team pushed and supported each other in ways they didn’t realize.

Mid-pandemic I was approached about an opportunity in the startup world. I was hesitant because this was not a pond I had swam in before. Was I ready to move on to a new team and build from the ground up? While this opportunity quickly didn’t make sense, I did get introduced to the fractional model that many startups and small businesses were using. Access to top talent on a fractional bases all while feeling that you have them full time. Brilliant but could this actually work for sales?

This brought me down a rabbit hole as to the resources for sales leadership that startups have. As a startup founder, you are the first to sell and statistically, you do not have any sales experience. Fast forward you are ready to hire a head of sales. Now you have the traditional model of a very expensive head of sales that is rep #1. They likely don’t have true leadership experience or the ability to actually scale and grow the business or the sales team. Then what? There is also cringy stereotypes that are sadly not that off about the salesy head of sales that has left so many founders burned.

Meet Rebel Scout Consulting. Providing fractional sales leadership to startups and small businesses! We support founders in the early days of founder-led sales all the way to hiring and growing the sales team or steps in in the absence of a sales leader while the CEO peruses the lengthy search of a new head of sales. Sales had slowed or plateaued but things feel foggy. Rebel Scout Consulting comes in to support business analysis and the creation and execution of a strategic growth plan. We have had the honor of driving millions in growth, sales team development and leading sales and impacting personal and career growth in ways I didn’t realize when I founded. This is truly the resource many startup founders lack and I am pumped we are creating a fun, impactful and approachable way to grow.

What’s worked well for you in terms of a source for new clients?

Word of mouth! The specialty of fractional sales leadership is niche and nothing encourages a CEO to have the initial conversation than a recommendation.

What’s a lesson you had to unlearn and what’s the backstory?

The corporate world is full of guardrails and bureaucracy. Things take time and creativity is stifled. There is a sensitivity around new ideas and a seemingly black-and-white way of doing things. Que crumbling up the paper and spiking it into the trash can.

Time to roll up the sleeves and know there are very few limits. Entrepreneurs are Rebels, hence the businesses’ name. We break the rules and find the way. We’re resilient and stop at nothing to succeed. In the early days and meetings, I was not getting the initial traction I had anticipated. CEOs were hesitant and looking back so was I. I didn’t want to appear I’d come in like a bull in a china shop. I wasn’t connecting the dots of how this would all work. Who would do what? How would sales and marketing would interact. etc.

Contact Info:

• Website: www.rebelscout.co
• Linkedin: www.linkedin.com/in/hilarynswan