SaaS & Tech Sales Prompts

You are a solutions consultant helping a sales rep prepare for a discovery call with a technical buyer.

CONTEXT:
- Prospect's role: [ROLE - e.g., CTO, VP Engineering, Tech Lead]
- Company: [COMPANY NAME]
- Industry: [THEIR INDUSTRY]
- Our product: [YOUR PRODUCT/SERVICE]
- Known tech stack: [ANY KNOWN TECHNOLOGIES THEY USE]

Generate 10 discovery questions that:
1. Demonstrate technical credibility (not surface-level)
2. Uncover real pain points in their current architecture/workflow
3. Avoid sounding like typical sales qualification questions
4. Lead naturally toward problems our product solves
5. Show genuine curiosity about their technical challenges

Format each question with:
- The question itself
- Why this question matters (what you're trying to learn)
- A natural follow-up question based on likely answers

You are a solutions engineer helping handle a technical objection.

THE OBJECTION:
"[PASTE THE TECHNICAL OBJECTION - e.g., 'We could build this ourselves in a few sprints']"

CONTEXT:
- Our product: [YOUR PRODUCT]
- Their company size: [EMPLOYEE COUNT]
- Their engineering team size: [IF KNOWN]
- Known technical concerns: [ANY CONTEXT]

Provide:

1. ACKNOWLEDGE & VALIDATE
- Show you understand why this is a reasonable concern
- Reference similar situations you've seen

2. REFRAME THE CONVERSATION
- Shift from build vs buy to total cost of ownership
- Highlight hidden complexity they may not have considered

3. SPECIFIC COUNTER-POINTS
- 3-4 concrete technical points
- Include specific questions to ask that expose complexity

4. BRIDGE TO VALUE
- Connect back to their core business goals
- Show how time saved = competitive advantage

5. SUGGESTED RESPONSE
- A conversational paragraph you can use verbatim

Help me prepare for a technical integration discussion with a prospect.

THEIR ENVIRONMENT:
- Primary tech stack: [LANGUAGES/FRAMEWORKS]
- Key systems to integrate: [CRM, ERP, DATA WAREHOUSE, etc.]
- Authentication: [SSO PROVIDER IF KNOWN]
- Compliance requirements: [SOC2, HIPAA, etc.]

OUR PRODUCT:
- Product: [YOUR PRODUCT]
- Integration options: [API, WEBHOOKS, NATIVE INTEGRATIONS, etc.]

Generate:

1. INTEGRATION ARCHITECTURE QUESTIONS
- 5 questions to understand their integration needs
- Questions that show you understand enterprise complexity

2. COMMON INTEGRATION PATTERNS
- 3 typical integration approaches for companies like theirs
- Pros/cons of each approach

3. POTENTIAL BLOCKERS TO ANTICIPATE
- Security/compliance concerns
- Data residency questions
- Performance/latency requirements

4. PROOF POINTS
- Types of similar integrations you should reference
- Questions to ask about their timeline and resources

Write a cold email to a developer or engineering leader that doesn't trigger their "sales email" detector.

PROSPECT:
- Name: [NAME]
- Role: [ROLE]
- Company: [COMPANY]
- What they build: [THEIR PRODUCT/SERVICE]

YOUR PRODUCT:
- What it does: [PRODUCT DESCRIPTION]
- Technical differentiation: [WHAT MAKES IT SPECIAL]
- Relevant pain point: [PROBLEM YOU SOLVE]

CONSTRAINTS:
- No buzzwords (synergy, leverage, revolutionize)
- No fake personalization ("I love your company!")
- No vague claims without specifics
- Keep it under 100 words
- Sound like an engineer, not a marketer

Write 3 versions:
1. Direct problem-focused approach
2. Technical curiosity angle
3. Peer-to-peer (engineer to engineer) tone

For each, include subject line and brief rationale.

Write an email to convert a freemium user to a paid plan.

USER DATA:
- Name: [NAME]
- Company: [COMPANY]
- Time on free plan: [DURATION]
- Usage: [KEY METRICS - features used, frequency, etc.]
- Hitting limits: [ANY LIMITS THEY'VE HIT]

PAID PLAN BENEFITS:
- Key features they'd unlock: [LIST]
- Price point: [PRICE]

APPROACH:
Don't be pushy. Instead:
1. Acknowledge their usage and what they've accomplished
2. Identify a specific unlock that would help them
3. Make the upgrade feel like a natural next step
4. Include a specific, low-friction CTA

Write the email in a conversational, helpful tone. Max 150 words.

Write a cold email to someone using a competing product.

PROSPECT:
- Name: [NAME]
- Role: [ROLE]
- Company: [COMPANY]
- Current solution: [COMPETITOR THEY USE]

COMPETITIVE INTEL:
- Known weaknesses of competitor: [LIST]
- Why customers switch: [COMMON REASONS]
- Our key differentiators: [LIST]

RULES:
- Never trash-talk the competitor directly
- Lead with curiosity, not assumptions
- Focus on outcomes, not features
- Acknowledge switching costs

Write 2 versions:
1. Problem-aware (they may not know there's a better way)
2. Solution-aware (they're actively evaluating alternatives)

Include subject lines and explanation of approach.

Help me map and strategize a multi-stakeholder SaaS deal.

DEAL CONTEXT:
- Company: [COMPANY]
- Deal size: [ARR]
- Product: [WHAT WE'RE SELLING]
- Timeline: [EXPECTED CLOSE]

KNOWN STAKEHOLDERS:
[List each person with: Name, Role, Attitude (Champion/Neutral/Blocker), Notes]

UNKNOWNS:
- Who else needs to be involved?
- Who controls budget?
- Who has veto power?

Generate:

1. STAKEHOLDER MAP
- Visual representation of influence/authority
- Identify gaps in our coverage

2. INDIVIDUAL STRATEGIES
- For each stakeholder: what they care about, how to engage
- Specific value props by role

3. RISK ASSESSMENT
- Where are we weak?
- Who could derail this deal?

4. ACTION PLAN
- Next 3 moves to strengthen our position
- How to multi-thread without stepping on toes

Help me navigate enterprise procurement for a SaaS deal.

DEAL STATUS:
- Company: [COMPANY]
- Champion: [NAME]
- Deal value: [ARR]
- Verbal yes from: [WHO APPROVED]
- Now in: [PROCUREMENT/LEGAL/SECURITY REVIEW]

KNOWN BLOCKERS:
[Any specific concerns or requests from procurement]

TIMELINE PRESSURE:
- Our deadline: [DATE AND WHY]
- Their fiscal year/budget cycle: [IF KNOWN]

Generate:

1. PROCUREMENT PLAYBOOK
- Common SaaS procurement requests
- How to handle each efficiently

2. LEGAL REDLINE STRATEGY
- Typical enterprise contract pushback
- What to concede vs. stand firm on

3. CHAMPION ENABLEMENT
- How to arm your champion to push internally
- Talking points for their procurement team

4. ACCELERATION TACTICS
- How to speed up without being pushy
- Creating urgency that benefits them

Create a renewal strategy for a SaaS account.

ACCOUNT:
- Company: [COMPANY]
- Current ARR: [AMOUNT]
- Contract end: [DATE]
- Tenure: [YEARS AS CUSTOMER]

HEALTH INDICATORS:
- Usage trends: [UP/DOWN/STABLE]
- Support tickets: [VOLUME AND SENTIMENT]
- NPS/CSAT: [IF KNOWN]
- Champion status: [STILL THERE? ENGAGED?]

EXPANSION POTENTIAL:
- Unused licenses/features: [LIST]
- New use cases identified: [LIST]
- Org changes that create opportunity: [LIST]

Generate:

1. RENEWAL RISK ASSESSMENT
- Score 1-10 with rationale
- Key risk factors

2. 90-DAY RENEWAL PLAN
- Timeline of touchpoints
- Who to engage and when

3. RENEWAL CONVERSATION FRAMEWORK
- How to open the discussion
- Handling price increase conversations
- Expansion opportunities to introduce

4. SAVE PLAYS (if at-risk)
- Concessions to consider
- Value reinforcement strategies