Anamika Mandal is a fintech leader and commercial strategist who most recently served as North American commercial lead for Cash App and Afterpay at Block. Prior to Block, she led business development and partnerships at Robinhood, where she oversaw partnerships across investment products including brokerage, retirement, community stock programs, IPO access, and directed share programs.
Mandal also serves as a mentor on sales, business development, and go-to-market strategy at First Round's Fast Track program. She joined Mercury Raise to share insights on evolving sales strategy from founder-led motions to enterprise-scale operations.
Navigating post-acquisition integration
When Anamika Mandal joined Block as North American commercial lead for Cash App and Afterpay, she stepped into a critical inflection point: Block had just completed its $29 billion Afterpay acquisition, and the buy-now-pay-later platform needed to transition from startup-style growth to enterprise-level scalability and profitability.
“They had found product-market fit and scale, but the next step was really thinking about the path to profitability,” Mandal explains. Her mission went beyond just integrating Afterpay's business. She needed to reimagine how the platform could leverage Block's broader ecosystem, including Cash App and Square, while maintaining the startup agility that drove its initial success.
The three pillars of sales philosophy
This experience led Mandal to her current philosophy on the evolution of sales strategy as companies mature. It centers on three key elements: audience focus, substantive communication, and compelling style. “‘You’ is the most powerful word in sales language,” she notes. “People love to hear about themselves.” This means you should “research your prospect, know them, know their pain points.” And if you don’t, then you should “ask and be very curious about what's going on in their world” — well before any pitch.
SMB vs. enterprise: strategic considerations
For early-stage founders assessing whether to focus on SMB or enterprise markets, Mandal advocates for prudent usage of resources. While enterprise logos can provide crucial credibility, she warns that these sales cycles are “long, complex, and typically involve multiple stakeholders.” And large enterprises often expect substantial discounts, despite their marquee status.
In contrast, SMB sales cycles move faster with higher volume, though they tend to be more price-sensitive. “It could be a hedge play in different environments,” Mandal explains. “The subscription fees that you might get from scaled SMB are great, but could be more volatile in nature. While landing an enterprise client can take longer, of course, these can be great deals to win that stick around for a longer period of time.”
Building the sales function
When transitioning from founder-led sales to building a dedicated function, Mandal emphasizes that timing is everything. The key trigger is achieving product-market fit, but she cautions that founders need to ensure they have bandwidth for proper management and training before making that first sales hire.
This transition represents a critical inflection point that many founders rush into prematurely. Beyond just having the budget for a sales hire, companies need established processes, clear documentation of what’s working, and most importantly, the capacity to properly onboard and mentor new team members. When evaluating that first sales development representative (SDR), Mandal emphasizes looking beyond just experience metrics.
“It's around thinking about: does this individual have experience selling at a similar deal size market and someone actually you would want to buy from,” she advises. The distinction is subtle but important: technical sales experience matters, but equally crucial is finding someone who can authentically represent your brand and build the kinds of relationships that will define your sales culture as the team grows.
Education and onboarding strategy
For products requiring significant customer education, Mandal recommends focusing first on the onboarding experience. “That onboarding is like the first interaction one has with your product,” she explains. “Delivering excellent customer support is very critical.” She advocates for multiple learning formats while maintaining transparent communication throughout the process.
The individual-to-enterprise journey
A particularly nuanced challenge she's tackled is converting individual users to enterprise customers. Her approach centers on understanding why individual champions love the product and identifying how those benefits scale to team environments.
“Having a few of those champions and really understanding why they love it, what they're finding useful that helps them in their day-to-day tasks and activities is crucial,” she explains. This insight should then inform both product development and sales strategy to encourage natural collaboration and team adoption.
Building long-term relationships
Mandal has found that successful long-term relationships often hinge on providing value beyond the core product. This could mean making strategic introductions, sharing relevant industry insights, or inviting prospects to events. “This isn't a transaction; it's a relationship,” she emphasizes.
Comprehensive GTM strategy
For founders looking to develop a comprehensive go-to-market strategy, Mandal outlines five essential elements:
- Deep market understanding that goes beyond surface-level competitor analysis to identify genuine user pain points
- A clear value proposition that resonates with specific customer segments, rather than trying to be everything to everyone
- Effective marketing channels that align with where your customers actually spend their time
- Well-defined sales processes that scale
- Measurable objectives that track customer success and product stickiness
She particularly stresses the importance of documentation and building feedback loops into each of these elements, both of which can help ensure a continuous analysis of customer feedback to refine the approach.
This emphasis on systematic feedback collection becomes especially crucial as companies scale: where founders might start with informal check-ins and ad hoc feature requests, growing companies need more structured ways to gather and act on user insights.
Formalizing user feedback
As startups scale, Mandal suggests considering a client advisory board to formalize feedback channels with early customers. At E-Trade, she saw how this approach helped build a committed user base even as a third-place player in the market.
“People love to give advice and feedback,” she notes. While cautioning to take input “with a grain of salt,” she's found that involving users in product development can create powerful evangelists who accelerate adoption within their networks.
From managing complex enterprise relationships at Block and Robinhood to developing scalable SMB processes at E-Trade, Mandal has developed a framework that helps founders evolve their sales strategy. Her approach emphasizes that while sales motions may become more sophisticated over time, success ultimately hinges on understanding your audience deeply and maintaining authentic relationships — whether you're selling to a pre-seed startup or a Fortune 500 company.
Phoebe Kranefuss