How to Sell Without Sounding Like a Salesperson | Courtany Williams | Ep. 298 (Lead)
Mar 27, 2025
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Courtany Williams, Director of Growth Sales at Insightly, shares her expertise in upselling and cross-selling strategies. She emphasizes the importance of tailoring demos to specific customer needs and encourages a collaborative approach in sales discussions. Courtany introduces the technique of inviting prospects to visualize solutions, enhancing trust and engagement. Additionally, she discusses the value of confirming customer buy-in before advancing discussions and how aligning next steps with customer goals can drive effective sales outcomes.
Effective upselling relies on understanding existing customers' interactions with services to identify tailored product opportunities.
Collaboration between sales teams and Customer Success Managers is crucial for aligning customer goals and maximizing upsell potential.
Deep dives
Identifying Growth Ideal Customer Profiles (ICPs)
Developing an effective growth strategy begins with identifying the appropriate Ideal Customer Profiles (ICPs). It is essential to differentiate between growth ICPs and new business ICPs, as the two have varying needs and characteristics. Growth ICPs focus on existing customers and their potential for upselling various products based on factors like company size and product usage. For instance, targeting VPs of marketing becomes crucial when exploring cross-sell opportunities into marketing automation solutions for customers who have already purchased a CRM.
Leveraging Customer Engagement
Understanding how existing customers interact with a company's services can reveal valuable upsell and cross-sell prospects. By optimizing points of engagement, like support queries, sales teams can identify opportunities to introduce additional features or products that align with customer needs. Training support representatives to recognize these moments can significantly impact lead generation; for example, customers who frequently seek assistance with email functionalities could be perfect candidates for a marketing automation tool. This proactive approach not only enhances customer satisfaction but also drives growth.
Weekly Deal Reviews for Improvement
Implementing structured deal reviews can significantly enhance the sales process and uncover valuable insights for managing accounts. During these meetings, Account Executives can present complex deals, allowing peers and leadership to contribute ideas and solutions. This collaborative environment fosters better decision-making and can identify new product offerings that might address customer challenges, ultimately enhancing the likelihood of closing deals successfully. For instance, discussions may reveal integrations that resolve specific issues and create opportunities for cross-selling additional products.
Training and Collaboration for Sales Success
Effective collaboration between Customer Success Managers (CSMs) and sales teams is vital for maximizing sales potential within existing accounts. Regular joint meetings ensure that both teams are aligned on customer goals and current standings, allowing for seamless upsell conversations during quarterly business reviews (QBRs). Training programs geared toward product knowledge and market needs empower sales representatives to address customer pain points effectively and position additional or upgraded products as solutions. Additionally, incentivizing CSMs to facilitate leads can create a unified front in managing customer accounts and expanding sales opportunities.
KPIC + Make Them Hold It: In demos, tie each feature to the prospect’s problem, impact, and desired change—then ask them to visualize how they’d use it in their world.
Assume, Don’t Assert: Instead of saying “we can solve this,” say “assuming we can solve this, what would change?” It builds trust and invites them into the solution.
Confirm Before Next Steps: Before talking price or next calls, ask if they believe it solves their problem. If they say yes, follow up with “what stood out to you?”
Tie Next Steps to Their Goals: Frame multithreading as being in their best interest. “To solve this, we’ll need [person] on board. How can we make that happen?”