Ep 206: Prospecting That Actually Feels Natural with Jenna Deyle
Selling isn't a personality trait. It's a system.
Sales envy is real. You watch someone effortlessly book meetings, build relationships, and "just know what to say," while you stare at a blank LinkedIn message and wonder if you're cut out for this.
Jenna Deyle spent more than 15 years in industrial distribution sales before starting Level 3 Sales Coaching, where she trains and upskills B2B sales teams. Her whole approach is built on behavior change, because that's the only way she's seen real results stick.
We talked about what prospecting actually means, her LinkedIn-first outreach approach, and the (delightfully nerdy) Notion + Todoist + Claude workflow that keeps her pipeline full without living inside a CRM.
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Prospecting isn't marketing
Marketing and prospecting work together, but they aren't the same job.
Marketing builds awareness with a lot of people at once. Prospecting is the active, one-to-one work of starting conversations with the specific people you want to work with. And cold outreach? That's only one slice of it. Warm outreach, networking, and following up with people who already know you all count too.
Jenna's take on the "rules" of sales: there aren't any hard and fast ones. There's a science and there's an art, and your job is to figure out what works for you, your personality, and your client base.
Keep prospecting when your plate is full
This is the trap I see constantly. Client work gets busy, prospecting is the first thing to slide, and a few months later the projects wrap up and the pipeline is empty.
Jenna's fix is to make outreach a routine instead of a mood. Every week she has a set number of warm LinkedIn reach-outs, cold requests, and networking requests due by Thursday. She can do them whenever during the week, but they have to get done.
A LinkedIn-first approach that earns replies
Jenna walked through how she actually does outreach on LinkedIn, including:
When to send a connection request with no note at all
How to open with something personal that earns a reply (instead of a pitch)
Why most B2B outreach needs about seven touches across channels before a prospect is ready to meet
Why a fast "no" is actually a win
That last one is a big mindset shift. A quick no frees you up to focus on the people who are a real fit, instead of chasing someone for months.
Lead with value using trigger events
The easiest way to make outreach feel natural is to have a real reason to reach out. Jenna looks for trigger events like:
Google News alerts on companies and people she's watching
Role changes and promotions
Seasonal planning cycles
Simple shared context, like a mutual connection or a post they wrote
When you show up with something relevant, you're not interrupting. You're continuing a conversation.
The workflow nerd section
This is where we went full nerd (in the best way).
Jenna exports her LinkedIn network and uses Claude to help prioritize who to reach out to. She also talked about multithreading, meaning building relationships with more than one person inside an account so a deal doesn't live or die with a single contact.
Then there's her CRM, which she built in Notion and barely has to open. After a call, she talks through her notes, action items, and next follow-up date, and Claude updates the record for her. Every Sunday, Claude reviews her client pipeline, speaking pipeline, and networking hub, flags anything due in the next seven days, and pushes those follow-ups into Todoist so nothing falls through the cracks.
She wrote about both tools on her Substack if you want the full breakdown:
The biggest thing to remember
You don't need to be a natural salesperson. You need a system that fits your real life: your busy weeks, your client work, and your personality. Build the routine, lead with value, and let your tools handle the remembering.
What part of your prospecting workflow do you want to simplify first?
Jenna Deyle
Jenna Deyle spent over 15 years in industrial distribution sales before pivoting to start her own business training and upskilling B2B sales teams. She believes focusing on behavior change is the only way to see real results, and the name of her company, Level 3 Sales, reflects just that. She settled in the Kansas City area almost five years ago after multiple cross-country moves during her corporate career. She is an active part of the KC community and is proud to call it home for herself, her husband, and her one-year-old daughter.
