246 (Lead) Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

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

ACTIONABLE TAKEAWAYS: Leverage Twitter for Outreach: Use X (formerly Twitter) creatively to direct prospects to your personalized email. Vin records and tweets videos at CMOs to grab their attention. Smart Follow-Up Strategies: If emails aren’t opened, start a new thread. If they’re being opened, reply to the same thread to keep your outreach efforts visible. Cold Email Framework: Craft emails with an observation, the problem, a solution, and a clear call to action for maximum impact. Use Unique Triggers for Follow-Ups: Don’t repeat the same email. Write four emails based on different research triggers to keep your outreach relevant and engaging. VIN'S PATH TO PRESIDENT'S CLUB: Founder @ CreatorBuzz Senior Account Executive @ DemandBase Account Executive, Mid-Market @ DemandBase Enterprise Business Development Rep @ DemandBase RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Schedule regular meetings with your champion to maintain deal momentum and reduce scheduling friction Schedule multiple next steps simultaneously if they're not dependent on each other to accelerate the deal. Determine whether the prospect will present, ask, or inform the board about the purchase, and prepare accordingly. Ask your champion questions that they might not know, prompting them to involve higher-ups who can provide answers. SAM'S PATH TO PRESIDENTS CLUB: CEO @ Sam Sales Head of Enterprise Sales @ LinkedIn Vice President North America Sales @ ON24 RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: 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. Consistent Review Rhythm: Reps update pipelines Monday, managers review Tuesday, deal reviews happen Wednesday, and Eleanor finalizes calls Thursday. ELEANOR'S PATH TO PRESIDENTS CLUB: - Head of Sales @ Retool - Global Head of Commercial Retention & Regional Director of Commercial Sales @ Segment - Global Head of Commercial Renewals and Retention @ Segment - Head of Customer Success and Solutions engineering @ Clever Inc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal