Meet the team that’s modernizing the RFP process

Weston Lunsford
CEO
Weston brings years of experience as an operator, investor, and leader in the SaaS world.  Weston drives our vision and strategy, ensuring that Plansight remains at the forefront of innovation in the employee benefits space.
Chris Toyn
CFO
With his extensive experience in finance and accounting, Chris plays a critical role in driving our financial success and growth. His strategic insights and financial expertise enable us to make sound business decisions and optimize our operations for maximum efficiency.
Steve Overton
FOUNDER | CPO
Steve oversees all aspects of Plansight, with a particular focus on the software platform. Steve’s decades of experience in the employee benefits industry brings unrivaled insight to the product for both brokers and carriers.
David Sitterud
FOUNDER
Dave works hand-in-hand with our broker and carrier partners to ensure success on all sides. His work on both broker and carrier technologies gives our product and clients a leg up.
Nick Warner
EVP OF CLIENT SUCCESS
Nick leads our customer success team with a proven track record in onboarding and supporting clients successfully in the software world. With his expertise and dedication to our client’s success, Nick ensures that each client receives the best possible experience.
Avatar photoAvatar photoAvatar photo

Join the Plansight team

If you have experience in the insurance industry and are passionate about
using technology to improve lives, we’d love to meet you!
6 min read

The Broker's New Moat and the Art of Social Selling

Based on Episode 5 of the Benefits Broker Boost Podcast with Adam Smith and Sims Tillirson.

Executive Summary

In this episode of The Benefits Broker Boost Podcast, host and Plansight CMO, Adam Smith, sat down with social selling expert Sims Tillirson to break down the new rules of broker growth. In an industry where technological moats are rare and acquisitions are common, the individual broker is now the moat

Sims explains why brokers must shift away from high-volume, low-converting outbound methods and instead focus on highly targeted, omni-channel outreach all centered on building genuine connections on platforms like LinkedIn. The key to winning inbound leads is to teach, not tell, in your content and measure impact by Revenue, not vanity metrics.

The takeaway is clear: brokers who rethink their processes and adopt more innovative tools will position themselves as strategic partners, not just renewal processors.

The Problem: When Outbound Fails

The traditional, high-volume outbound strategy of cold calling and mass emailing is no longer effective. As Adam noted, fake customization is rampant, leading to inbox fatigue for decision-makers.

Sims highlights that global outbound success rates are currently about 1%. Brokers continue to engage in mass outreach despite knowing:

  • Mass Personalization is a Myth: "It does not exist. It does not work".
  • The Guard is Always Up: The first impression is often negative when a pitch is forced.

Instead, Sims argues it is far better to send 50 very targeted outreaches using higher-converting methodologies than 1,000 generic emails.

For a fresh approach that trades cold calls for connection, check out this previous discussion on Thinking Outside the Box.

The Blueprint: Mastering Omni-Channel and Pattern Disruption

The solution for brokers is a shift to less outbound and a focus on high-converting first-touch methods that disrupt the buyer's pattern. Every successful campaign today must be omni-channel, including direct mail, LinkedIn, cold calling, and cold emailing.

High-Converting First Touches

Sims noted that two high-effort, high-reward methods significantly outperform the global 1% success rate:

  • Direct Mail: Converts at about 10% on the first touch to a meeting. This involves sending "provocative or evocative" items, such as a fake obituary or a missing persons report, to lower the prospect's guard for the follow-up cold call.
  • Video DMs: Convert closer to 20%. This is a massive pattern disruption, as most C-suite decision-makers receive zero to one video DMs per week.

The best example of this pattern disruption involved a broker who used a video DM followed by a custom-bound children's book featuring the prospect's face. This sequence resulted in a 30% meeting book rate with large life groups.

The LinkedIn Flywheel: Four Pillars of Growth

For brokers building their presence, Sims outlined the four pillars required for LinkedIn's algorithm, which rewards reciprocity:

  1. Expand (Network Growth): Send 10 to 20 blank connection requests daily to your target buyers.
  2. Engage (Thoughtful Interaction): Leave at least 10 thoughtful comments daily on prospect posts to further conversations and ensure your content appears in their feed. Also, use soft-touch DMs to start conversations.
  3. Educate & Entertain (Content): Post daily content that teaches, not tells. Avoid "feature dumping" about your brokerage, as the "moat is you". Write case studies as stories and use personal interests (guitars, fitness) to build a connection.
  4. Elevate (Move Offline): Send at least five video or audio DMs daily, asking for a meeting to move the conversation from "one to many" to "one to one".

Measuring What Matters: Revenue, Not Vanity

Many brokers chase viral posts, but Sims warns that the two most viral posts he ever wrote generated zero dollars. The metrics that matter are those tied directly to Revenue:

  • Saves and Sends: These are the best indicators that a prospect is sharing or bookmarking your content, signaling an imminent deal.
  • Tracked Clicks: Use links within your posts to drive traffic and track direct clicks to your website or lead magnets.

As Adam summarized, this focus shifts from the excitement of a viral post to ensuring a direct connection to actual Revenue.

"I still get the best results when I hire a personal trainer, even though I know, I know exactly what they're going to do... but that accountability is going to get me better results," said Adam, illustrating why the disciplined process of social selling works even when you know the theory.

Final Thought: The Time to Act is Now

Sims offered a powerful final thought for those hesitating on social selling: "You may think you've been left behind today because you haven't started, but if you look up in five years and you're not doing this, you're probably going to be looking for another job."

Adam echoed this sentiment, stating, "I watched it adapt and I watched companies flourish and I watched companies struggle because they didn't. And LinkedIn is... on the very early end of that for what happened with Facebook." The industry is at the very front end of this wave, and the brokers who adopt, learn, and promote their personal brand, their moat, will be the ones who flourish.

The time saved by scaling smarter with AI directly enables the high-effort, high-reward strategies needed for success on LinkedIn.

👉 Schedule a discovery call with a specialist to learn how Plansight's technology can free up your team to focus on the high-value strategic conversations required for social selling.

Book a Demo

About Plansight

At the end of the day, Plansight is more than just software. It is a partner built with brokerages and their benefits teams in mind. From SmartSheetingAI™ to RFP automation to side-by-side comparisons to the intelligence of PlansightAI, everything we create is designed to lighten the load, reduce risk, and elevate your client relationships.

Your team is your greatest asset. Plansight is here to make sure they have the tools, insights, and support to shine. For brokers, Plansight is the only complete end-to-end renewal and marketing solution that transforms a manual, time-consuming RFP process into one that is fast, efficient, and more profitable.