268 (Lead) How To Run a "Land & Expand" The Right Way (Eleanor Dorfman, ReTool)

ACTIONABLE TAKEAWAYS Prioritize Storytelling: Assess storytelling skills during interviews and coach reps on it. It's a foundational human communication skill that drives sales success. Evaluate Questions Asked: Learn as much from the questions a rep asks as you do from their answers. It reveals their curiosity and understanding. Mock Pitch Preparation: Let candidates pitch your product with basic information provided, such as target personas, company size, and common challenges. Avoid setting them up to fail. Grade with Context: When evaluating candidates, adjust expectations. Benchmark them one level lower than your top AEs to account for their lack of product knowledge. ANDREWS'S PATH TO PRESIDENTS CLUB: Head of Sales @ Superhuman Sr Director of Sales @ Scale AI Head of Global Email Sales & GTM @ Twilio Manager Enterprise Sales @ Twilio RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Leverage POC Momentum: Initiate vendor review at the POC’s peak excitement. Parallel process legal and finance steps to accelerate the deal. Involve Executives in POCs: Require VP-level involvement for POCs. Share examples of risks when executives are excluded to build alignment and trust. Confirm POC Entry Criteria: Secure problem agreement, power alignment, and price understanding before starting a POC to avoid misalignment. Set Realistic Exit Goals: Use achievable metrics, like output benchmarks, within the POC timeframe. Avoid long-term criteria that extend beyond the POC. DEREN'S PATH TO PRESIDENTS CLUB SVP of Sales @ JustCall VP WW Sales @ Ambassador Labs Global Head of Data Analytics Sales @ Google Head of Looker North American Sales @ Google RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS If you make a mistake while recording a prospecting video, don't discard it. Send it anyway, as it can add authenticity and still lead to positive outcomes. When you feel the conversation winding down, go straight to asking for the meeting to increase your chances of booking it. After sending a LinkedIn video, start by asking, "What did you think of the video?" followed by "What didn't you like about the video?" to engage prospects. Leverage your last interaction—whether it's a video, voicemail, or previous call—as the reason for your next outreach to create continuity and context. PATH TO PRESIDENT’S CLUB Sales Director @ Pareto Senior Business Development Manager @ Pareto Senior Account Executive @ Pareto Account Executive @ Pareto Business Development Representative @ Pareto RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

Get your forecasting resources ACTIONABLE TAKEAWAYS Commit Deal Essentials: Reps must report four details for commit deals: dollar amount, close date, economic buyer, and their engagement. If not engaged, share the plan to involve them. Three Forecast Methods: Use a top-down pipeline view, a bottoms-up deal analysis, and AI tools for better forecast accuracy. Combining these improves reliability. Quarterly Milestones: By month one, secure 50% of forecasted deals. Month two should see 60% closed, leading to 100% by month three. Prioritize Best Case Deals: Spend less time on commits with clear criteria. Focus on best-case deals and strategies to convert a few more into wins. TAYLOR'S PATH TO PRESIDENTS CLUB: VP of Sales @ Xactly RVP, Sales - NA Growth & Commercial @ Xactly RVP, Sales - West & NA Growth Head of GTM @ roOomy RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Streamline Proposals: Remove unnecessary features to cut costs and stand out from competitors with bloated quotes. If prospects need a feature, they’ll request it, giving you control to reintroduce it strategically. Ask Questions on RFPs: Use RFP responses to ask about priorities and requirements, opening the door for discovery and tailoring your response to their needs. Disqualify Early: Disqualify deals if your product isn’t a fit or their problem seems like a “nice-to-have.” Identifying this early saves time and lets you focus on better opportunities. Test Product Gaps: If a feature is missing, ask how critical it is to their goals. Confirm whether this gap is disqualifying or if the deal can move forward. JOHNNY'S PATH TO PRESIDENTS CLUB Commercial Account Executive @ Talkdesk Enterprise Sales Development Manager @Talkdesk Team Lead, Enterprise Sales Development @ Mimeo Enterprise SDR @ Mimeo RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Give Johnny a Follow

FOUR ACTIONABLE SALES TAKEAWAYS During demos, connect features shown to insights gathered during Discovery. Address confusion promptly and facilitate discussions rather than relying on your Solutions Consultant. Make your effort visible to prospects when working on the business case. Let them know you're actively involved and invite collaboration, which fosters reciprocity. Refine and finalize your business case incrementally. Use the demo to make the case tangible and save detailed financial discussions for the final business case meeting. When negotiating and faced with a request for a discount, refrain from immediate responses. Silence can be powerful as it prompts the prospect to reconsider or elaborate on their request. PATH TO PRESIDENT’S CLUB Enterprise Account Executive @ Webflow Senior Account Executive @ Webflow Account Executive @ Webflow Senior Corporate Account Executive @ Udemy RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

Mark and Armand walk through the steps needed to provide effective ongoing training to your sales team. ACTIONABLE TAKEAWAYS Use a capability & cognitive load matrix to decide what to focus your training on The best person for the job to be running that training and sales enablement is the most respected rep or manager on the team Train your managers before you train your teams Establish existing weekly rhythms then drop the reinforcement into one of those existing rhythms so you're not adding new meetings RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Ask for Competitor Proposals: If a prospect cites competitor pricing, request their proposal to directly compare offerings and address discrepancies. Rank Negotiation Priorities: When prospects negotiate on multiple factors, ask them to prioritize what matters most, then focus concessions on top-ranked items. Meet Two Key Pricing Criteria: Share pricing only when the prospect acknowledges your solution addresses a critical pain and they influence or approve purchasing decisions. Create a Cost for Discounts: When asked for a discount, request the prospect to identify features or services they are willing to remove, framing concessions as a trade-off. JOHNNY'S PATH TO PRESIDENTS CLUB Commercial Account Executive @ Talkdesk Enterprise Sales Development Manager @Talkdesk Team Lead, Enterprise Sales Development @ Mimeo Enterprise SDR @ Mimeo RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal How to finish a negotiation in one cut

FOUR ACTIONABLE TAKEAWAYS Explore two types of impact with your prospect: hard metrics (e.g., hours spent, money lost) and soft impact. Address pain points in other departments to accelerate deals and improve win rates. Turn situations into problems by asking questions that highlight known pain points with competitors. If ghosted late in the deal cycle, offer to email the next key contact directly to prompt a response. PATH TO PRESIDENT’S CLUB Account Executive @ Webflow Account Executive @ SafeGraph Account Executive @ Procore Technologies RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Uncover what’s not working: Use varied questions in one-on-ones, like “If you had a magic wand, what would you change?” or “Where have we let you down in the sales cycle?” to surface actionable feedback. Run radical candor sessions: Gather reps for skip-level feedback on their manager. Facilitate discussions on what the manager should keep, stop, or start doing, and provide actionable feedback to the manager for growth. Stay connected with the team: Conduct regular skip-level meetings, whether quarterly one-on-ones or group discussions, to maintain trust and understand team challenges directly. Lead with strategic priorities: Focus on 2-3 key quarterly initiatives, like improving prospecting systems or revamping coaching processes, to drive long-term business impact beyond daily operations. STEPHANIE'S PATH TO PRESIDENT'S CLUB: VP of Global Sales at PandaDoc Chief Revenue Officer at Sprig Chief Revenue Officer at FlowHub VP of Sales, SMB at Glassdoor RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal