Deal winning process

Deal winning process

When to use

Use this skill when:

• The company is a "must win" or competitive deal
• You need to help the partner close with founder trust + speed
• You need a structured win plan (value + process + narrative)
• You're competing against other funds for a deal

Inputs you should request (only if missing)

• Who else is in the round (competitors, likely lead)
• Founder priorities (price vs partner vs speed vs brand)
• Your firm's intended role (lead/​follow) and constraints
• Timeline (term sheet date, decision date)
• What the founder is optimizing for (explicitly ask)

Outputs you must produce

1. Win plan (one page with daily actions)
2. Founder decision criteria (written down, not guessed)
3. Value preview list (3 concrete actions you can deliver in 48 hours)
4. Competitive positioning (why us vs each competitor, in founder's language)
5. Process timeline (meetings + diligence + decision date + term sheet)

Templates:

• assets/​win-plan.md
• assets/​value-preview.md

Core principle: Win by doing, not by pitching

The best way to win a competitive deal is to demonstrate partnership before asking for the deal. Value previews > pitch decks.

Procedure

1) Identify the founder's decision criteria (ASK, DON'T GUESS)

Ask directly:

• "What does a great partner do for you in the next 6-12 months?"
• "What are you optimizing for in this round (speed, price, control, help)?"
• "What would make you not choose us?"
• "How are you making this decision? What's the process?"
• "Who else are you talking to and what do you like about them?"

Write the criteria down. If you can't articulate what the founder is optimizing for, you will lose.

2) Build a one-page win plan (with daily actions)

Include:

• Why us (2 bullets, in founder's language)
• What we will do in the next 7 days (specific deliverables)
• Who at the firm is involved (right people, not a parade)
• Timeline with dates
• Risks the founder is worried about + how you address them

3) Do value previews BEFORE asking to win (within 48 hours)

High-signal previews (pick 2-3 that match founder priorities):

Rules:

• Make offers you can fulfill within 48 hours.
• The offer must be specific: "I'll intro you to [Name] at [Company] who runs [function]" not "I can make intros."
• Close the loop: "Did that help? What else is blocking?"
• Track what you offered and what you delivered.

4) Run a clean process (founder-centric)

• Send agendas before every call.
• Consolidate diligence asks into one request.
• Keep partner time high-quality: pre-wire internally; no surprises.
• Don't posture about leading if you aren't.
• Never miss a deadline you set.

5) Competitive positioning (in founder's language)

For each competitor:

Never trash competitors. Acknowledge their strengths, then pivot to your differentiated value.

6) Handle terms responsibly

• Be explicit about what you can offer and what you can't.
• If you're using time pressure, ensure it's real; fake deadlines destroy trust.
• If terms are the deciding factor and you can't win on terms, pivot early: "We're not going to be the cheapest. If price is the deciding factor, you should take their deal."
• If terms aren't the deciding factor, don't lead with terms.

7) Track and iterate (daily during competitive process)

Daily check-in questions:

• What did we deliver today?
• What does the founder need tomorrow?
• What's blocking the decision?
• Is our timeline still accurate?
• Did anything change with competitors?

Salesforce logging (recommended)

• Update Opportunity with competitor set in Notes.
• Log value-preview actions as Activities with outcomes.
• Track next step and owner per action (Tasks with due dates).
• Update Opportunity stage as you progress.

Use salesforce-crm-ops for API patterns.

Win / loss tracking (post-decision)

After every competitive deal (win or loss):

• Document why we won / lost (founder's words, not your interpretation)
• What value previews resonated?
• What would have changed the outcome?
• Update win plan template based on learnings

References

• Feld/​Mendelson public writing is useful for what terms matter and how to keep terms "simple."
• Mark Suster is useful for fundraising dynamics and board mechanics.

Edge cases

• If another firm is leading: your job is to be the best co-investor. Prove it with concrete help, not promises.
• If the founder is optimizing for brand: your best lever is credible operator help + partner fit, not hype.
• If you're losing on terms: decide early whether to compete or gracefully exit. Don't drag it out.
• If the founder is non-communicative: ask directly "Are we still in this process? What would we need to do to be your choice?"