What was the problem/opportunity?

Most sales content is created for sales teams swimming upstream (toward enterprise) or purely for SEO purposes with a bounce-worthy level of keyword stuffing throughout.

There was a huge competitive gap for quick, actionable content assets that spoke directly to the needs of B2B SaaS SMB Account Executives who ran full-cycle sales processes. Build around topics they talked about where they hung out (LinkedIn), not solely focused on high-volume keywords.

The Account Executive Playbook was built for that purpose.

Who were we talking to?

• Champions: Sales managers & team leads who hear about Pickle frequently & will mention problems we solve when new sales enablement software is top of the buyers mind or when their contract is up with our competitor.

  
  

• End users: B2B SaaS SMB Account Executives with a full-cycle sales process. They’re looking for an edge in any deal & want to be prepared before during and after every meeting.

What was the mission?

Pickle was always rooted as the champion for end users (SMB full-cycle AEs selling over Zoom). This content pillar was built to provide un-gated value & further cement our position as the only Conversation Intelligence tool AE’s need before, during, and after meetings.

How was success measured?

The was meant to be a long-term brand positioning play & demand capture into our owned channels. Success was measured by LinkedIn referral traffic, opt-in newsletter conversions, and demo bookings.

• Tracking & attribution were done through Google Analytics, MailerLite, Intercom, SalesLoft, Typeform, Salesforce, and AirTable. Used Zapier to connect them all.

What was the outcome?

• 274.42% increase YoY in target referral traffic (LinkedIn & Google)

• Pickle's LinkedIn following grew to 3,800+

• Our Brine Newsletter subscriber increased 978.27% YoY in top-funnel subscribers topping at around 6k subs.

• Saw a 41.22% increase YoYin demos booked, visit-to-demo conversion rate was around 4.37%/month avg.

• 62% of total ARR attributed to demand generation campaigns & ABM programs

What was the strategy/distribution plan?

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

Customer Activation Assets

• Personalized kickoff/onboarding meetings that set each user up for immediate “aha” moments & create stickiness faster.

• Email & in-app chat automation feature highlights, product how-to’s, referral program opportunities, etc.

• Ongoing invites to training, events, giveaways, content collabs, etc. we were doing.

Bottom Funnel Assets

Pain & solution-aware landing pages based on topics like competitor comparisons, specific integrations, etc. outlining all the points from above. All were linked within follow-up messages to know who was landing on them.

The goal was to have them book demos or start free trials after building enough trust throughout the top funnel experience. Self-attribution like the inbound demos below were a big part of our measurement:

Mid Funnel Assets

Captured top-funnel demand with our Brine Newsletter signups, Sales Meeting Analyzer & events.

ABM Efforts: Outbound campaigns built around peer prospecting (AE to AE) & pre-recorded demos that address specific pain points. These were sent after a hand-raise engagement from the top funnel to ensure higher quality.

Templates for stakeholder mapping, meeting agenda templates, etc. that are tied back into the Pickle product features full cycle sellers cared most about.

Top Funnel

Un-gated content all maximizing your effectiveness as a seller before, during, and after your meetings: How to prep/train, open, qualification, discovery, demo, objections, etc. Helps them tackle the topics they care most about while we plug Pickle screenshots along the way positioning as the solution.

Social selling on LinkedIn:

Utilizing the content we created, our sellers built personal brands while positioning Pickle as a key tool for their success. ‘Eating our own dog food’ so to speak. Reactions/comments to posts would move into the mid-funnel for more targeted engagement.