How to close $100K+ enterprise deals, step by step | Jen Abel
Jen Abel details a 15-step enterprise sales cycle, from landing the first meeting to navigating procurement and closing deals, offering a tactical playbook for B2B SaaS. This guide emphasizes deep learning, co-creation, and strategic project management.
Deep Dive Analysis
45 Topic Outline
Introduction to Enterprise Sales Cycle
Why Share Enterprise Sales Playbook
Case Study: Selling AI Legal Tech to SpaceX
Step 1: Landing the First Meeting
Targeting Executives and N-1
Crafting the Alpha-Driven Message
Pincer Model for Outreach
Finding N-1 Contacts and Outreach Channels
Iterating on the Pitch
Step 2: Running the Intro Call
Importance of the Intro Call
Informal, Dialogue-Focused Approach
Extracting Information and Identifying Needs
Disqualifying Unqualified Leads
The Art of Sales vs. Scripted Approaches
Step 3: Running a Follow-Up Call
Avoiding Direct Demo Post-Intro
Building Rapport and Co-Authoring the Demo
Pre-Demo Strategy and Intel Gathering
Step 4 & 5: Prepping and Running the Demo
Tailoring the Demo to Stakeholders
Focusing on 20% of Product for 80% Value
Enterprise Sales as Project Management
Step 6: Post-Demo Debrief
Immediate Feedback from Champion
Identifying Potential Deal Killers
Step 7-9: Preparing for and Running the Pilot
Defining Pilot Success and User Tasks
Two-to-Three Day vs. Longer, Charged Pilots
Pre-Pilot Discussion on Deal Closure Timeline
Pricing Discussions Post-Demo
Standard CRM Pipeline vs. Real Sales Process
Step 10: Post-Pilot Session
Gathering User Feedback and Syncing with Champion
Identifying Red Flags and Losing Momentum
Healthy Enterprise Win Rates and Pricing Strategy
Step 11-14: Navigating Procurement and Signature
Papering Prep and Setting Procurement Timeline
Papering Review and Live Legal Calls
Procurement Process and Negotiation Tactics
Step 15: Signature
Thinking About Expansion Post-Signature
The Role of Services in Enterprise Sales
How Buyers Can Say No Gracefully
Enterprise Sales as Product Management
6 Key Concepts
Alpha (in Sales)
The unique, differentiating, and often counter-intuitive advantage or insight your product provides that helps an executive achieve significant, needle-moving impact beyond standard problem-solving. It's the unfair advantage you offer.
Pincer Model
A sales strategy involving simultaneous outreach to both the top executive (e.g., Chief Legal Officer) and their direct report (N-1) within an organization to create parallel interest and alignment.
Information Edge
The competitive advantage gained by actively listening and extracting detailed, nuanced information about a prospect's specific priorities, challenges, and internal dynamics to tailor the sales approach.
Champion (in Sales)
An individual within the client organization who is highly invested in seeing your solution implemented and actively helps navigate the internal decision-making process as an internal advocate.
Enterprise Win Rate
The percentage of qualified sales opportunities that result in a closed-won deal in enterprise sales, typically 25-35%, with higher rates potentially indicating underpricing.
Papering
A term used in enterprise sales to refer to the legal contract and associated documentation involved in closing a deal, encompassing drafting, review, redlining, and negotiation.
8 Questions Answered
Most people mistake the five-stage CRM pipeline (intro, demo, proposal, contracting, closed) as the actual sales process, when in reality, these are merely buckets for forecasting, and the true cycle involves closer to 15 detailed steps.
You should target either the top executive (e.g., Chief Legal Officer) or their direct report (N-1), as these individuals hold the necessary budget and influence to move a deal forward.
The most important aspect is to keep it informal, avoid demos or slides, and focus entirely on listening and extracting as much information as possible about the prospect's needs and desired changes, as they will be less open later in the process.
No, you should not record initial sales calls because it can make prospects less open and vulnerable, hindering the collection of crucial, unfiltered intelligence.
A healthy win rate for enterprise deals, from qualified lead to signed contract, is typically between 25% and 35%. If your win rate is significantly higher, it might indicate that your product is underpriced.
Pricing discussions should ideally happen post-demo, but before the pilot, and should be conducted one-on-one with your internal champion. Work with them to build the business case and defend the value, rather than immediately offering discounts.
Buyers should explain as soon as possible why the timing is not right or why their organization lacks the maturity to adopt the technology, rather than ghosting or making excuses.
Services can be a significant part of enterprise deals, as large organizations are accustomed to buying them and often have dedicated budgets for consulting, implementation, or custom work, even for software companies.
20 Actionable Insights
1. Target Executive and N-1 Simultaneously
Focus outreach on the top decision-maker (e.g., Chief Legal Officer) or their direct report (N-1) using a ‘pincer model’ to ensure the message reaches those with budget and influence from multiple angles.
2. Craft Alpha-Driven Pitch
Develop a 2-3 sentence message that highlights the unique ‘alpha’ or unfair advantage your product unlocks for the executive, going beyond problem-solving to offer needle-moving impact.
3. Prioritize Learning on Intro Call
Conduct the initial 30-minute intro call informally, without demos or slides, focusing entirely on understanding the prospect’s priorities, challenges, and desired changes to extract maximum intelligence.
4. Avoid Recording Intro Calls
Do not record the initial intro call to encourage openness and vulnerability from the prospect, fostering a more genuine and informative dialogue.
5. Disqualify Unfit Prospects Quickly
Be prepared to disqualify prospects if their organizational maturity or needs don’t align with your product’s value, typically one in four calls, to save time and focus efforts on viable opportunities.
6. Co-Author Demo with Champion
Before the main demo, have a 15-30 minute follow-up call with your internal champion to collaboratively plan the demo, identify key stakeholders, and determine what aspects of the product will resonate most.
7. Narrow Demo Focus
During the demo, only showcase the 20% of your product that delivers 80% of the value relevant to the prospect’s specific needs and priorities, avoiding extraneous features that could dilute the message or raise pricing concerns.
8. Conduct Immediate Post-Demo Debrief
Immediately after the demo, debrief with your internal champion to get their raw reaction, identify potential deal killers, and strategize on how to address any concerns or engage quiet stakeholders.
9. Define Pilot Success Jointly
For pilots, co-author clear success metrics and specific tasks with the prospect, ensuring users know exactly what to do and how value will be measured, preventing aimless exploration.
10. Time-Box Short Pilots
For light-lift solutions, limit pilots to 2-3 days and focus on core user tasks to quickly demonstrate value and accelerate the sales cycle.
11. Charge for Extended Pilots (with Credit)
If a pilot requires significant integration or a longer duration (e.g., 1-2 months), charge for it, but offer to credit the fee back if the deal moves forward, signaling serious buyer intent.
12. Pre-Empt Procurement Early
Before the pilot, discuss the timeline for getting signatures and identify key stakeholders like procurement and legal leads. This proactive approach addresses potential friction points early.
13. Offer Your Contract as Word Doc
When sending contracts, provide your paper as a Word document and offer the option to use their paper. This flexibility can accelerate the legal review process.
14. Address Redlines Live
For extensive contract redlines, schedule a live call with their legal team to discuss and resolve issues directly, rather than engaging in lengthy email exchanges, speeding up negotiations.
15. Create Urgency with Incentives
Offer a small incentive (e.g., a free month) for signing by a specific date to create urgency and motivate the internal team to push the deal through procurement and legal.
16. Negotiate Pricing Collaboratively
When discussing pricing, work with your champion to build the internal business case and defend the value. If they push back, ask for their help in figuring out how to make it work, rather than immediately offering discounts.
17. Understand Buyer’s Maturity
If a deal is stalling, assess if the buyer’s organization is truly mature enough to adopt your technology. Sometimes, it’s better to pause and revisit when they are better prepared.
18. Embrace Services for Enterprise
Be open to offering services as part of your enterprise solution, as large organizations are accustomed to buying services and often have dedicated budgets for them.
19. Avoid Sales Scripts
Do not rely on generic sales scripts (e.g., BANT questions) as they commoditize your approach and feel artificial; instead, focus on active listening and adapting your message.
20. Project Manage the Sales Cycle
Treat enterprise sales as a tight project management exercise, owning the narrative and framing at each step to guide the client through their buying process efficiently.
9 Key Quotes
The whole game is to slow down, to go fast.
Jen Abel
The most successful salespeople are not trained salespeople.
Jen Abel
The fastest way to commoditize yourself is to go into some sales script.
Jen Abel
Enterprise deals are one on this feels so close to who we are. It feels like it was built specifically for me. That's the whole game.
Jen Abel
The amount of times enterprises are like, hey, I'm not, I don't know if we want to spend this much money for half the tool that we wouldn't use half the tool. Now, all of a sudden you've just unraveled all the work you've just done.
Jen Abel
Enterprise sales is super, super, super tight project management. It's super, super tight narrative and framing, owning that frame, owning that frame to exactly who these people are.
Jen Abel
If your win rate is higher than that, your price is too low.
Jen Abel
Procurement's job is not to kill the deal. It's just to make sure that it is aligned with how they need to buy.
Jen Abel
You are a liability, not closing this gap.
Jen Abel
1 Protocols
Jen Abel's 15-Step Enterprise Sales Cycle
Jen Abel- Identify and target the top executive (C-suite) or their N-1 (direct report) for initial outreach.
- Conduct an informal, 30-minute intro call focused on listening and extracting prospect priorities, without demos or slides, and do not record it.
- Schedule a 15-30 minute follow-up call with your internal champion to co-author the demo plan and gather intel on stakeholders.
- Tailor the pitch and frame the demo specifically for the audience, especially for new attendees.
- Run the demo, focusing on the 20% of the product that delivers 80% of the value relevant to their specific priorities.
- Immediately debrief with your internal champion post-demo to get raw feedback and identify potential deal killers.
- Identify 3-4 power users for the pilot (not C-suite) and define clear success metrics and specific tasks for them.
- Before the pilot, discuss the desired timeline for getting signatures and identify procurement and legal leads.
- Run the pilot: 2-3 days for light-lift solutions, or 1-2 months (charged, with credit) for technical integrations.
- Gather feedback from pilot users and sync with your champion to understand their experience and address issues.
- Document the agreed-upon closing timeline and send your contract as a Word document, offering the option to use their paper.
- Review redlines; for extensive changes, schedule a live call with their legal team to discuss and resolve issues directly.
- Engage with the procurement lead and legal team on a live call to work through remaining questions or non-negotiable points.
- Identify the final signatory (e.g., CFO) and ensure your internal champion is aware to facilitate timely signing.
- Post-signature, involve the founder for early customers to understand custom needs and explore expansion opportunities, including offering services.