268 (Lead) How To Run a "Land & Expand" The Right Way (Eleanor Dorfman, ReTool)
Nov 28, 2024
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Eleanor Dorfman, Head of Sales at Retool, has a remarkable track record, growing the company to $100 million ARR in just four years. She shares insights on structuring sales teams to maximize both acquisition and expansion. Eleanor discusses the importance of a 'land and expand' strategy, emphasizing internal advocates and demonstrating ROI. She highlights systematic deal inspections and a consistent review rhythm to keep the sales pipeline efficient. Plus, learn how structured compensation plans can enhance customer retention and align team incentives.
Implementing a structured approach to deal inspection ensures accountability and preparedness for significant deals at critical stages.
Integrating retention into compensation plans incentivizes collaboration between teams, promoting client satisfaction and long-term loyalty.
Deep dives
Programmatic Deal Inspection
Establishing a structured and programmatic approach to deal inspection is essential for maintaining a well-executed sales process. Inspections are initiated at critical deal stages, specifically when a deal over $50,000 enters stage three or stage five. Early stage reviews address key factors such as readiness for proof of concept and understanding the competitive landscape, while late-stage reviews focus on mutual action plans and risk mitigation before closing. This approach not only helps to ensure that the team is prepared but also fosters accountability among team members in advancing significant deals.
Customer Retention Incentives
Integrating customer retention into the compensation plans of Account Executives is crucial, especially post-2022 when retaining customers has become increasingly important. By tying a portion of the compensation to retention rates, sales teams are incentivized to ensure that they are setting customers up for success right from the initial discovery call. This comprehensive approach encourages collaboration between pre-sales and post-sales teams, ensuring that all parties share the responsibility for retaining clients. For instance, at Segment, retention incentives were structured so that churn directly impacted sales quotas, promoting a holistic focus on client satisfaction and loyalty.
Team Structure and Sales Motions
Differentiating between market segments is key to an effective sales strategy, particularly in managing team structures for down-market versus upmarket accounts. In down-market accounts, a clear distinction is made between land and expand teams; the land team focuses solely on acquiring new logos, while the expand team handles account retention and growth. Conversely, upmarket teams adopt a cradle-to-grave approach, where Account Executives manage both the acquisition and retention of corporate clients, ensuring alignment across the sales lifecycle. This tailored approach allows the organization to optimize efficiency and maintain strong client relationships.
Effective Communication and Alignment
Fostering consistent communication and alignment across teams is vital as a sales organization scales. Regular 15-minute standups every Monday serve as a platform for teams to share updates on closed deals, renewals, and pipeline generation, creating a unified direction for the week. Celebrating achievements through a culture of public praise encourages motivation and morale, while discussions of challenges promote collective problem-solving. This emphasis on collaboration and transparency equips teams to hit their targets more effectively while cultivating a strong team culture.
Segmented Team Structure: Down-market teams focus on landing new logos, passing them to expand teams, while up-market AEs handle both acquisition and expansion with retention-based comp.
Enterprise Sales Strategies: Use top-down (sell wall-to-wall) or land-and-expand approaches, with the latter yielding higher LTV by scaling through business units first.
Deal Inspection Triggers: Monitor $50K deals at stage 3 for POCs and access to power, and stage 5 for mutual action plans and the paper process.