Calendly is expanding beyond its core scheduling function to address the full meeting process. They are developing solutions for meeting preparation, in-meeting engagement, and post-meeting follow-ups. This strategy of expanding horizontally around a core user problem illustrates a powerful path for SaaS growth.
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To shift a services-oriented company to a product mindset, frame productization as a competitive advantage. Repeatable, productized solutions offer greater market differentiation than purely custom builds, leading to more effective competition and new deal wins. This tangible benefit helps secure buy-in from sales and leadership.
Founder Tope Awatona created Calendly after experiencing personal pain in his sales role. He was losing valuable momentum with prospects due to the time-consuming back-and-forth of scheduling, which on average takes 7.6 emails per meeting. This highlights how solving a high-friction business problem can lead to a successful product.
A key expansion strategy is moving 'upper funnel' from treating specific, acute conditions to offering a holistic, preventative platform. For Hims & Hers, adding diagnostics ('Labs') created a new entry point for users to understand their overall health, not just solve one problem.
As software commoditizes, the buying experience itself becomes a key differentiator. Map the entire customer journey, from awareness to renewal, and design unique, valuable interactions at each stage. This shifts the focus from transactional selling to creating a memorable, human-centric experience that drives purchasing decisions.
Calendly's research reveals a paradox: while the common sentiment is anti-meeting, a vast majority (81%) of professionals believe more productive meetings would help them at work. This suggests the problem isn't the quantity of meetings, but their quality and purpose. People crave effective, decision-oriented collaboration.
Don't force your sales team to learn and sell a completely new product. Instead, integrate the new capability into an existing, successful product, making it "first" or "default" for that channel. This reduces sales friction and complexity, leveraging established momentum for adoption.
To grow an established product, introduce new formats (e.g., Instagram Stories, Google AI Mode) as separate but integrated experiences. This allows you to tap into new user behaviors without disrupting the expectations and mental models users have for the core product, avoiding confusion and accelerating adoption.
Avoid the trap of building features for a single customer, which grinds products to a halt. When a high-stakes customer makes a specific request, the goal is to reframe and build it in a way that benefits the entire customer base, turning a one-off demand into a strategic win-win.
Your calendar is the foundation of your execution system. Use AI to scan your schedule, find recurring blocks for deep work on key goals, and automatically suggest rescheduling conflicts. This moves AI from a passive assistant to an active agent that defends your most valuable resource: your time.
Move beyond selling features by offering a "Business Process as a Service" (BPaaS) solution. This involves contracting directly on the business outcomes clients care about, such as cost savings or revenue optimization. This model delivers an end-to-end capability and aligns your success directly with your customer's, creating a powerful value proposition.