Account Executive

May 26, 2022

Episode #02 Highlights: Maggie Blume

👋 No Follow Up…No Deal

How I Deal Episode #02 - Spotify & Apple

Maggie Blume takes Taylor & Junior through an epic inbound lead journey. Stretching over a year, but led to a solid closed-won deal. Utilizing her own platform, Mailshake, Maggie built personalized nurture sequences to keep the buyers engaged until the timing was perfect.

Have a deal in your pipeline with a distant targeted close date? Deploy Maggie's tips on the pod today to stay top of mind & unlock the deal next stage!

Guest Feature

Maggie Blume is an Account Executive @ Mailshake. She began her career as a staff accountant but made the switch to sales as an SDR.

After climbing the sales ladder at a previous company, she climbed about the Mailshake rocket ship as one of the original SDR hires and hasn’t looked back since!

Maggie Blume
Maggie Blume

What problem Does Mailshake Solve?

Helping B2B sales pros get in front of more qualified leads while prospecting. Leveraging Mailshake’s simple, yet powerful, platform, reps can automate mindless outbound tasks & help them generate higher-quality conversations.

Deal Details

Where did they come from?

  • Inbound lead via the website.

Company type

  • A growing insurance company.
  • 60 total employees. ~15 agents/reps (end-users).
  • Reps were a mix of brand new hires & very tenured pros.

Deal Length

  • Very long. Over a year.

Barriers to Overcome

  • Creating more urgency on a buyer’s timeline.
  • Staying top of mind throughout the process using a targeted drip campaign.

Buyer types

  • Users: agents who operate as full-cycle sellers.
  • Champion: a newer agent who spotted an issue with their prospecting email process.
  • Decision Maker: The champions manager

Episode Highlights

*Note: timestamps correlate with full conversation

Discovery: Inbound leads are not a given. Usually more competitive.

(8:05) “Nice! A demo just booked on our site. Quick demo time & send over the contract.”

While sometimes this is the case, it’s a terrible idea to start the first meeting this way.

Inbound leads can be like the Wild West. It feels predictable, you have no idea where they’re coming in their buyer’s journey.

They could have just read a couple blogs & wanted to learn more. Or they could be on their 10th demo with your competitor & just wanted to check out “one more alternative”.

Your inbound form probably won’t tell you this info.

Maggie approached her inbound lead with an open mind & ran a proper discovery conversation on their first meeting.

She learned the lead was an internal champion who was brand new to the company & to sales enablement software as well.

Here’s what she learned:

Follow Up: Sales timelines are never perfect. Follow-up holds it all together.

(11:25) In a perfect world, your sales cycle looks like this:

  • Find the prospect via LinkedIn (or they come inbound)
  • Hit ‘em with some personalized outreach, they love it & book time on the calendar.
  • You meet with the decision maker & dig up a lot of pain in initial discovery.
  • You run a pain-specific demo with every stakeholder.
  • They all agree this solution will solve their problems & they have the budget to buy it today.
  • The buyer signs the contract. You hit quota & can spend the rest of the quarter kicked back.

Sounds perfect! Well it’s a dream for a reason. Deals rarely go that smoothly. Things happen.

In Maggie’s case, the initial meeting with the champion in October 2020 went really well but the timing was off. The next meeting didn’t happen for another 7 MONTHS (June 2021).

What did Maggie do in all that time to stay top of mind? She created & maintained her own relevant follow-up drip campaign.

Here’s what happened:

Demos: No prospect is exactly the same. Why the hell are your demos?

(14:34) We have a saying around here at Pickle: “No pain, no demo.”

If there isn’t a defined pain or need for your solution (or at least a specific part of it), then it’s impossible to drive real value with a personalized demo.

It becomes a canned, feature-dump screen share that glazes the eyes of everyone involved.

Maggie even goes as far as feeling “uncomfortable” if she’s giving a feature-filled demo to a buyer that only needs to leverage one aspect of her platform.

Listen to how she describes giving three different demos during this deal:

3 Tips to Fellow Account Executives

1. You’re on your buyer's timeline.

While there are always ways to create urgency; ultimately the buyer decides what's next.

The best you can do:

  • Keep things simple by giving them one decision to make during each conversation.
  • Create more value around your solution or urgency on how much a problem is costing them.

But always follow their lead.

2. No follow-up, no deal.

We covered this above but to reiterate:

Outbound or inbound? Doesn't matter. Stay in touch consistently throughout the sales process.

Don’t just “any thoughts?” your prospect to death. Instead, always add more value.

3. Always have a Champion.

Of course, the decision-maker's needs are important; but strong relationships with the end-users are crucial.

The best buyers to work with are the ones that put faith in their lower-level employees to make informed recommendations about what to purchase that will make everyone's lives easier.

Identify those individuals who have that trust & build the relationship.

Watch the full conversation

You'll like these emails 🥒

Pickle writes to their friends every few weeks with spicy tips to make their wall-to-wall meetings suck less.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.