Brand-Dishing It Out with Plum | AI, creativity, & building an unforgettable brand

Introduction

In this webinar hosted by Praveen Das (Co-founder, Factors) and Aditi Shinde (Brand and Social Lead, Factors), Shreyas Achar, CMO of Plum, shares his playbook on building an unforgettable brand in a highly commoditized industry. The session covers Plum's philosophy of using creative, non-incremental brand bets to stand out, their approach to balancing long-term brand building with short-term pipeline demands, and how they are integrating generative AI into their creative workflows. Readers will learn how to establish trust with enterprise buyers, run high-risk creative campaigns, and navigate the trade-offs of AI-driven design.

About Shreyas Achar

Shreyas Achar is the Chief Marketing Officer at Plum, a 7-year-old corporate healthcare and insurance platform. Over his five years at the company, he has helped scale its services to over 6,000 businesses and more than 1 million members. Prior to joining Plum, Shreyas built his marketing career at Razorpay and CleverTap. He specializes in taking creative, non-incremental brand bets to make a historically commoditized, fear-driven industry simple, inclusive, and accessible.

Standing Out in a Commoditized Industry

• Intentional positioning: Plum chose a red logo to stand out in an industry where almost all competitors use blue, signaling a different approach to consultation, sales, and delivery.
• The three brand pillars: Every piece of content, campaign, and intellectual property Plum creates must align with three core values: making healthcare simple to understand, accessible to marginalized communities, and inclusive of all identities.
• Focusing on moments of impact: Shreyas's take is that the real brand team is customer success and support, as Plum's "aha moment" only happens to the 8% of the population that actually files an insurance claim.
• Ditching traditional collateral: Instead of standard corporate brochures and sales decks, Plum has sent out custom resumes to prospects saying "we want to join your team" and published children's bedtime storybooks.

Balancing the Buyer Persona with the End Beneficiary

• B2B2C brand approach: While Plum is a B2B organization selling to corporate decision-makers, they actively market to the end employees (Plum members) to drive utilization of benefits like mental health and doctor consultations.
• Humanize publication: Plum has run an independent digital publication called Humanize for over 2 years, releasing six articles monthly on sensitive workplace topics like paternity leave and caste in the office, with zero sales angles.
• Targeting intentional companies: Plum focuses on companies that view talent as their primary competitive advantage, rather than businesses that treat insurance as a compliance checkbox.
• The geographic brand skew: Shreyas jokes that Plum's brand is currently far better known in Bangalore's startup hubs like Indiranagar, Koramangala, and Whitefield than in the traditional enterprise corridors of BKC in Mumbai or Golf Road in Gurgaon.

Establishing Trust and Credibility with Enterprise Buyers

• The three-year enterprise sales cycle: Shreyas notes that converting an enterprise account takes three years on average: year one is for initial awareness, year two is participating in an RFP, and year three is getting an honest shot.
• Acting as a trusted intermediary: Because Plum connects buyers to large, regulated, and established insurance carriers, they carry less structural risk than a standalone startup product.
• Positioning as "nerds in the business": To counter traditional brokers who wear Savile Row suits and offer fancy entertainment, Plum's technologist founders position themselves as data-backed thinkers.
• Obsessive data reportage: Plum produces highly detailed 120-to-150-page reports, such as their "Standard of Employee Benefits" report, to establish intellectual authority among enterprise prospects.

The "FAFO" Creative Framework and Campaign Metrics

• The 80-10-10 time allocation: Plum's marketing team spends 80% of their time on core OKRs, 10% on enabling peers, and 10% on "FAFO" (F around and find out) projects that have no alignment with standard OKRs.
• Dedicated campaign resources: Plum has one team member whose sole responsibility is to execute one major creative campaign every single month.
• Measuring expressions of interest (EOIs): For campaigns launched outside of renewal cycles, Plum measures engagement friction—such as event attendance or benchmarking sign-ups—rather than direct CRM leads.
• The Nazar battu campaign: To build awareness for their asset and liability business insurance, Plum collaborated with students from the JJ School of Arts to hand-make and package traditional cultural symbols to ward off the evil eye, mailing them directly to business owners.

Taste-Maxing and Navigating the AI Design Debate

• In-house creative execution: Except for one external agency, Plum executes 100% of its creative, artwork, copywriting, and content production in-house.
• Scaling with Midjourney: When tasked with launching a new website requiring 73 distinct illustrations in one week, Plum's senior brand designer used Midjourney to find the perfect Style Reference (SRF) to generate the assets on time.
• The "taste-maxing" rule: Shreyas's rule of thumb is that AI tools must remain in the hands of top-tier craftspeople who maintain a high bar for design, preventing the output from looking like low-quality "slop."
• Surface area trade-offs: Plum uses AI for high-speed, short-lived growth assets like targeted social ads, but mandates hand-drawn illustrations for high-value assets like physical office posters and Humanize editorial art.

The Fable Social Media Experiment

• The Fable takeover: When Plum's social media manager, Krithin, went on a one-week vacation, the team handed the corporate LinkedIn account over to an AI agent named Fable, openly disclosing the experiment to followers.
• The human-in-the-loop reality: While Fable ran 90% of the account's activity, CTO Saurabh and Shreyas had to actively intervene in Slack to enforce brand guardrails and manage token usage.
• Unilateral goal focus: The experiment revealed that the AI focused too literally on its three programmed goals (doubling impressions, engagement, and followers), sacrificing the warm, friendly brand voice that human managers naturally maintain.
• Instagram automation: Following the experiment, Plum is testing AI-generated content on Instagram to prioritize daily posting consistency over sporadic human brilliance, though it has yielded only minor metric increases.

Conclusion

Building a memorable brand requires a willingness to take bold, non-incremental creative risks and step outside of standard industry playbooks. As Shreyas Achar and Praveen Das discussed, establishing long-term trust—especially with enterprise buyers—demands a mix of high-quality data reportage, consistent positioning, and empathetic customer experiences. While generative AI tools offer powerful ways to scale creative output and run fast experiments, maintaining human taste, editorial oversight, and transparency remains essential to preserving authentic brand equity.