What was the problem/opportunity?

The sales podcast world was filled with thought leaders talking purely theory or generic prospecting tips, while helpful, there was never a full picture painted of a deal from start to finish.

We filled that void with ‘How I Deal’. Each episode featured an interview with a real Account Executive about a single deal they worked on from start to finish. How they found it, worked it, and closed it.

Providing insight into how these sellers approach problems, run meetings, overcome objections, and hit quota. This further positioned us as the champion of full-cycle sellers & provided creative warm intros into our target accounts.

Also as the sole marketer at a startup, you need to find ways to repurpose pillar content across multiple channels effectively. Makes a small team feel bigger. How I Deal was my content well.

Who were we talking to?

• B2B full-cycle AE’s who wanted to learn how to improve their process

• Aspiring sellers who wanted insight into what it takes to succeed

• Sales leaders who want to train their reps on new strategies and each deal stage

What was the mission?

From a branding perspective, we wanted to be the full-cycle seller’s champion. From their go-to content source to their must-have sales enablement tool. Leading to more inbound demos.

How I Deal was also a core asset in our account-based marketing strategy. Bringing on sellers at target accounts we wanted to warm up & network into.

How was success measured?

Our North Star was qualified opportunities attributed to the podcast. Both inbound and outbound.

The secondary KPIs were based on listens and referral traffic to specific landing pages.

What was the outcome?

• Produced, hosted, edited, and distributed 49 episodes

• Generated an additional 16 qualified opportunities/month on average.

• A key factor in getting into two of our largest customers.

• Averaged 136 listens each episode & ~200 visits/week to our landing pages & shared Pickle recording pages (allowing visitors to experience the product).

• Top 10% of most shared podcasts globally in 2022 (Spotify)

What was the strategy/distribution plan?

I always plan from the bottom of the funnel & work up:

Customer Activation Strategy

Had guests on from recently closed customers & upcoming renewals. Helped build brand awareness for the company & highlighted the sales rep’s work on complex deals.

Furthering the relationship with the customer & the seller. This led to several repeat customers if the seller moved to another company.

Bottom Funnel Strategy

We planned strategic guest invites to sales reps at target accounts we were actively working or planning to penetrate in the next month or quarter.

Leveraging the sales process conversation we had with the seller as a way to understand how Pickle could help them & utilize their words in our warm outbound messaging to the decision makers. Leading to higher positive response rates and more qualified opportunities.

Mid Funnel Strategy

One of Pickle’s core value propositions was its effectiveness in capturing meetings & allowing users to jump to each highlight instantly.

I wanted to demonstrate that with the podcast recordings. Allowing solution & product-aware buyers to experience the Pickle platform in a non-salesly way.

I uploaded each episode into the Pickle platform, had it transcribed, created clips of the episode highlights & included the meeting recording UTM link along with other assets in every distribution channel.

Top Funnel Strategy

Launched each episode via multiple LinkedIn posts & Brine newsletter editions. Also, convert topics that got the most traction after launch into deeper dive posts and blogs. Allowing for multiple assets to be created from each episode.

We created a database on the website containing recap blogs that included highlight clips, episode topics, and full transcripts (thanks to Pickle).