Revolutionizing Outbound Sales with RevOps Expert Jacki Leahy

Jacki Leahy, a fractional RevOps advisor and founder of Activate the Magic, on the Hot Pursuit podcast. Jacki shared valuable insights on modern outbound sales strategies, the power of personalization, and how to navigate the challenges of today’s sales landscape.

From the Classroom to the Boardroom

Jacki has a highly unique perspective on sales. She started out as a kindergarten teacher before becoming a Business Development Representative. She points out that the skills developed in classroom management translate surprisingly well to sales and operations:

“Being a teacher, if anyone’s listening to this and you’re a former teacher, we have such a leg up on sales and operations, right? Because we have to have a process, classroom management, you have systems, you have process, and you train to the process.”

This background has allowed Jacki to approach sales operations with a fresh perspective, focusing on creating systems and processes that can be easily taught and replicated.

The Current State of Outbound

Jacki acknowledges that outbound sales is harder than ever, with challenges like:

  • Stricter spam and deliverability rules
  • Remote work making it harder to reach prospects
  • The proliferation of AI-generated personalization

However, she sees these challenges as opportunities to innovate and improve outreach strategies. Jacki emphasizes the importance of truly believing in your product or service:

“When you truly know that your product or service is going to change the game for that human, like, listen, let me get you promoted, kind of change making. When you truly believe that, then selling becomes service.”

Innovative Tools and Techniques for Personalized Outreach

Jacki shared several tools and techniques she uses to personalize outreach at scale:

  1. Clay: A tool that allows you to aggregate data from various sources and combine it into a single table.
  2. DISC Communication Style Framework: Used to tailor communication based on personality types.
  3. Crystal Knows: A Chrome extension that predicts DISC profiles based on LinkedIn profiles.
  4. AI-powered content creation: Tools like REAP for generating content snippets and ranking their potential virality.

By combining these tools, Jacki creates what she calls “operationalizing the scalpel” – a system that provides sales reps with all the information they need to personalize their outreach effectively.

Crafting Effective First Emails

When it comes to that crucial first email, Jacki takes a bold approach.

“That first email and cold outbound in general, you are interrupting someone’s day. So, if you’re trying to sidestep that or avoid that, you’re in for a bad time, right? And being triggering is the name of the game.”

She suggests using personality insights and industry knowledge to craft messages that are so interesting and compelling that they convert any initial offense into curiosity.

The Shift Towards Sustainable Growth

Jacki noted a positive trend in the industry towards more sustainable growth and a focus on human elements.

“I think we’re, as an industry, I think we are also shifting to focus on the humans, right? The shift from growth at any cost to sustainable growth and margins.”

This shift not only benefits customers but also creates a better environment for sales teams, moving away from the “growth at all costs” mentality.

Jacki’s Approach to RevOps Consulting

Through her company, Activate the Magic, Jacki helps businesses under 200 employees optimize their sales processes. She describes her ideal clients as companies that are “selling despite themselves” – those with great product-market fit but chaotic internal processes.

Her approach focuses on providing agile, nimble solutions:

“Goodbye ideal state and hello adequate, right? When you’re growing and you’re figuring things out, and that’s where I love to help with the tech stack and the HVAC and plumbing behind revenue teams.”

Key Takeaways

  1. Leverage your unique background and skills in sales operations.
  2. Embrace the challenges of modern outbound sales as opportunities to innovate.
  3. Use a combination of tools and frameworks to personalize outreach at scale.
  4. Don’t shy away from interrupting prospects’ days – make it worth their while.
  5. Focus on sustainable growth and human-centric sales processes.
  6. For growing companies, aim for adequate solutions that can be implemented quickly rather than perfect but slow-to-implement systems.

Jacki Leahy’s insights provide a fresh perspective on outbound sales, emphasizing the importance of personalization, agility, and human connection in an increasingly digital world. By embracing these principles, sales teams can navigate the challenges of modern outbound and achieve sustainable growth.

To learn more about Jacki’s approach or to connect with her, visit or find her on LinkedIn.