Are you a seasoned sales leader who’s driven rapid revenue growth and optimized sales functions on a part-time or contract basis? We want to hear from you! What we’re looking for: - A person with a track record as a fractional or interim Head of Sales, VP of Sales, or Sales Director Please answer the following questions: - At what stage of a company’s growth do you typically get brought in as a fractional sales leader, and why? - Which three metrics do you prioritize to measure success in a 3- to 6-month engagement? - What are the biggest misconceptions founders or boards have about fractional sales leadership?

Typically, I'm brought in as a fractional sales leader during the post-product-market-fit stage—right when a company starts seeing initial traction but struggles to build repeatable, scalable sales processes. At this point, founders often need to move from founder-led sales to a formalized structure, and that's where I help streamline systems, align GTM efforts, and develop early playbooks without the cost or risk of hiring a full-time executive. In a 3- to 6-month engagement, I prioritize three core metrics: Sales velocity - Are deals moving through the pipeline faster? Conversion rate by stage - Where are we losing momentum and why? Average deal size - Is the sales strategy attracting the right-fit customers or just inflating activity? One example: I worked with a mid-stage WordPress plugin development agency that had strong inbound leads but no structured sales follow-up. In under four months, we implemented a CRM workflow, trained two reps, and tripled the number of closed deals per quarter without increasing ad spend. The biggest misconception founders have is thinking that fractional sales leadership is only about plugging holes. In truth, it's about building foundations—strategy, hiring roadmap, sales enablement—so that growth is not only rapid but sustainable. Tip: Before bringing in a fractional sales lead, ensure you have clear goals, even if rough. Clarity accelerates results.

I've stepped in as a fractional sales leader a few times, so I know the rhythm well. At what stage I'm brought in: Usually when a company hits that messy middle—post-product/market fit but pre-scaling systems. They've proven people want the product, but the sales process is still founder-led, chaotic, and very manual. They bring me in to build the first real sales engine: hiring reps, setting up repeatable playbooks, and tightening the pipeline. Three metrics I prioritize: Pipeline Velocity (how fast deals move through stages) Conversion Rate by Stage (especially from first meeting to proposal) Sales Cycle Length (because long, unpredictable cycles kill scaling) Biggest misconceptions founders/boards have: Thinking a fractional leader will "just close deals" themselves instead of building a system that scales beyond them. Believing sales is a "short-term fix" when really, early sales problems usually expose deeper product, pricing, or positioning issues. Expecting hockey-stick growth in 3 months without investing in marketing, lead gen, or proper sales enablement. Fractional sales leadership isn't about being a superhero closer—it's about architecting sustainable revenue growth fast, then getting out of the way.

I usually get brought in as a fractional sales leader when a company has started making sales but doesn't have a proper system yet. The founder is often handling sales themselves, but it's becoming too much. They want to grow fast, but they don't have a clear process, and revenue is up and down. That's where I step in — to build structure and make things more predictable. In my first 3 to 6 months, I focus on three main things: 1. How fast deals move — If it's slow, there's usually something broken in the process. 2. Which channels bring the best customers — So we can focus on what works. 3. How quickly new sales hires can start closing deals — If it takes too long, we fix the training and setup. One of the biggest myths is that a fractional leader is just a temporary fix or someone to jump in and start selling. That's not the case. I don't just close deals — I build the sales system that others can run after I'm gone. Another common mistake is thinking I'll just come in and hire salespeople. But hiring without fixing the process first usually leads to more problems. The real value is in getting the basics right: clear messaging, strong systems, and a repeatable process that actually works.

My involvement as a fractional sales leader usually kicks in during key transition phases of a company's growth—often when a startup is ready to scale significantly or when an established company needs to revamp its sales strategies to break into new markets or recover from a slump. The timing is crucial as it allows me to leverage my expertise in building robust sales processes and teams that can swiftly adapt and drive rapid growth, aligning with the company's evolving goals. In my 3- to 6-month engagements, I prioritize three main metrics to measure success: revenue growth, pipeline health, and sales cycle length. Revenue growth is the clearest indicator of immediate impact, while pipeline health forecasts sustainability. The sales cycle length helps in identifying bottlenecks and inefficiency in the sales process. These metrics provide a comprehensive view of the sales function and are key to crafting strategies that yield long-term benefits. One of the biggest misconceptions founders or boards have about fractional sales leadership is that results can be delivered almost instantly without sufficient resources or proper alignment with broader company strategies. Often, there's an expectation for fractional leaders to be miracle workers who can turn around performance overnight. However, substantial results need time, strategic changes, and sometimes, cultural shifts within the company. In conclusion, fractional sales leadership is about strategic intervention at critical moments in a company’s lifecycle. It's essential for leadership and boards to have realistic expectations and provide the necessary support to truly harness the potential of fractional expertise in scaling their ventures effectively.

Right after the founder realizes they can't do it all themselves. Usually they're post-revenue, somewhere in the low millions or just trying to break through that wall. They've got leads, maybe a rep or two, but no real system. Deals are inconsistent, and they're tired of chasing instead of closing. That's when I show up—clean up the pipeline, fix the messaging, and lay a real foundation. Which three metrics do I track in a 3-6 month sprint? Simple: Qualified pipeline (because without it, nothing else matters) Sales velocity (are we speeding up or dragging?) Conversion rate from demo to close (if that's broken, no amount of leads will help) Everything else feeds into those. Biggest misconceptions founders or boards have about fractional sales leadership? They think I'm a glorified closer. I'm not. I'm there to fix what's broken, make the sales process repeatable, and help them stop hiring sales reps just to burn through leads. Another one—they expect immediate miracles. But if there's no product-market fit or the offer's all over the place, I'm going to tell them. I'm not there to babysit bad strategy. I'm there to fix it.

I typically get brought in when companies hit that crucial $1-2M ARR mark and need to build a scalable sales process, just like I did at CBDNerds when we needed to expand our reach. Founders usually reach out when they've got product-market fit but struggle to build repeatable sales processes, which is exactly when a fractional leader can make the biggest impact in establishing systems and training teams.

Having scaled Dirty Dough from scratch to 100 locations, I've learned founders often expect fractional sales leaders to be miracle workers who'll fix everything in 90 days, when really it's about building solid foundations. I focus on three core metrics - customer acquisition cost, conversion rate through the sales funnel, and average deal size - because these helped me validate our franchise model before expanding to 400 units.