Multi-Stakeholder Follow-Up Sequence: Post-Proposal (Aggressive)

Target Account: Fortune 500 Bank
Deal Stage: 2 weeks post-proposal
Strategy: Aggressive multi-threading with role-specific value messaging
Sequence Duration: 6 touchpoints over 14 days

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Stakeholder Map

CFO (Procurement Decision)

• Primary concern: ROI, budget allocation, risk mitigation
• Decision timeline: Slower (quarterly budget reviews)
• Messaging focus: Financial impact, payback period, risk reduction

CTO (Technical Evaluation)

• Primary concern: Integration complexity, security, scalability
• Decision timeline: Moderate (technical validation cycles)
• Messaging focus: Architecture fit, technical due diligence, implementation timeline

VP Sales (Use Case Owner)

• Primary concern: Team adoption, revenue impact, speed to value
• Decision timeline: Faster (operational pain point)
• Messaging focus: Sales team productivity, competitive advantage, quick wins

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Threading Strategy

Days 1-6: Individual 1:1 outreach with role-specific value
Days 7-10: Target VP Sales (fastest mover) with urgency
Days 11-14: Group accountability emails + direct questions

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TOUCHPOINT 1 (Day 1) - Individual Emails

To: CFO

Channel: Email (9:00 AM send time)
Subject: ROI model from our proposal - CFO review

Hi [CFO Name],

Two weeks since we submitted our proposal. I wanted to pull out the financials that matter most to you:

• $2.4M annual savings through process automation (page 8 of proposal)
• 6-month payback period based on your current cost structure
• 23% reduction in operational risk (compliance automation)

Given your Q2 budget review cycles, would it make sense to schedule 20 minutes this week to walk through the financial model? I can bring our CFO to address any questions about payment terms or multi-year structuring.

Three time slots that work: [Tuesday 10am], [Wednesday 2pm], [Thursday 9am]

Best,
[Your Name]

Why this works: Numbers-first approach, references proposal specifics, acknowledges CFO decision timeline, peer-to-peer offer

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To: CTO

Channel: Email (9:15 AM send time)
Subject: Technical diligence questions - CTO input needed

Hi [CTO Name],

It’s been two weeks since our proposal, and I’m guessing your team is in technical evaluation mode. Based on our demo discussions, I anticipate questions about:

1. API integration with your core banking platform
2. Data sovereignty (your EMEA requirements)
3. Security certifications (SOC 2 Type II, ISO 27001)

I’ve prepared a 15-page technical addendum that answers the 12 most common CTO questions we get from financial services companies. Can I send it over, or would you prefer a 30-minute architecture review with our Chief Architect?

Either way, what’s blocking technical sign-off on your end?

Best,
[Your Name]

Why this works: Anticipates technical concerns, offers immediate value (addendum), direct question, respects evaluation process

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To: VP Sales

Channel: Email (9:30 AM send time)
Subject: Your sales team’s 15% productivity gap - quick question

Hi [VP Sales Name],

Two weeks since the proposal. Quick recap of what this solves for your team:

Current state: Your reps spend 18 hours/week on manual data entry
Future state: Automation cuts that to 3 hours, giving them 15 hours back for selling

That’s effectively a 15% productivity increase without hiring. At your team size (80 reps), that’s 1,200 extra selling hours per week.

Straight question: Are you running into internal blockers (CFO budget, CTO security review), or is this a timing issue? I want to help you push this through if it’s still a priority.

15-minute call this week?

Best,
[Your Name]

Why this works: Operational pain focus, quantifies impact, acknowledges internal blockers, offers partnership

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TOUCHPOINT 2 (Day 3) - Different Channel (LinkedIn)

To: VP Sales ONLY

Channel: LinkedIn Message (2:00 PM)

Hey [VP Sales Name] - Tried email, thought I’d try here.

I know you’re slammed, but wanted to check: Is this still on your priority list, or should I focus on working with [CFO Name] and [CTO Name] to move it forward?

Totally fine either way - just want to make sure I’m threading this correctly on your end.

Why this works: Different channel, permission-based, multi-threading transparency, low pressure

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TOUCHPOINT 3 (Day 6) - Value-Add (No Ask)

To: All Three (Separate Emails)

Channel: Email (10:00 AM)

To CFO:
Subject: Thought you’d find this relevant - no ask

[CFO Name],

Saw this Deloitte report on financial services automation ROI (published last month). Page 14 covers payback period benchmarks for banks your size.

No ask here - just thought it might be useful context for your evaluation.

[Link to report]

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To CTO:
Subject: API integration reference - FYI

[CTO Name],

One of our banking clients (similar core banking platform to yours) just published their integration case study. Might answer some of your team’s architecture questions.

No call needed - just sharing in case it’s helpful.

[Link to case study]

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To VP Sales:
Subject: Sales productivity benchmark - thought of you

[VP Sales Name],

Gartner just released their 2025 sales productivity report. The section on “time spent selling vs. admin work” mirrors exactly what we discussed in the demo.

Sending it over in case it helps you make the internal case.

[Link to report]

Why this works: Pure value-add, no pressure, maintains visibility, role-specific content

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TOUCHPOINT 4 (Day 9) - Direct Pressure on VP Sales

To: VP Sales

Channel: Phone + Voicemail (10:30 AM)

Voicemail Script (35 seconds):

“Hey [VP Sales Name], [Your Name] here. I’ve reached out a few times - email, LinkedIn, now phone. Look, I get it - you’re busy, and this might not be the right time.

Here’s my question: Should I keep working with [CFO Name] and [CTO Name] to get this moving, or is there something blocking this that I don’t know about?

Just reply to my last email with a one-word answer - ‘yes’ if we should keep going, ‘no’ if it’s dead. Either way is fine, I just want to respect your time.

Thanks, [VP Sales Name].”

Why this works: Multi-channel persistence, direct question, multi-threading strategy, respectful exit option

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TOUCHPOINT 5 (Day 11) - Group Email (Accountability)

To: All Three (CC’d together)

Channel: Email (9:00 AM)
Subject: Proposal follow-up - need your input

Hi [CFO Name], [CTO Name], [VP Sales Name],

It’s been two weeks since we submitted the proposal, and I haven’t heard back from any of you. I’m looping you all in together because I know enterprise decisions involve multiple stakeholders.

Where we are:

• CFO: Financial model submitted (6-month payback)
• CTO: Technical diligence materials available
• VP Sales: Sales productivity impact quantified (15% gain)

What I need from you:

Can one of you reply with where this stands? Three options:

1. Still evaluating - I’ll follow up in [X days]
2. Need more info - Tell me what’s missing
3. Not moving forward - I’ll close the loop and follow up in 6 months

I don’t want to be a pest, but I also don’t want this to fall through the cracks if it’s something your teams need.

Best,
[Your Name]

Why this works: Group accountability, multi-threading visibility, direct options, respectful pressure

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TOUCHPOINT 6 (Day 14) - Break-Up Email (Individual)

To: All Three (Separate Emails)

To CFO:
Subject: Last note from me - [CFO Name]

[CFO Name],

This is my last email. I’ve tried multiple times over the past two weeks, and I haven’t heard back.

If the financial model doesn’t work, or if budget timing isn’t right, I completely understand. But if I could’ve done something differently to help you evaluate this, I’d appreciate the feedback.

If things change in Q3 or Q4, feel free to reach out. Otherwise, I’ll follow up in 6 months.

Best,
[Your Name]

P.S. - If you DO want to move forward, just reply “yes” and I’ll get us back on track.

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To CTO:
Subject: Final follow-up - technical evaluation

[CTO Name],

I’m closing the loop on this. If there are technical blockers I didn’t address, or if this doesn’t fit your architecture, I’d love to know what I missed.

Either way, I’ll stop reaching out unless I hear from you. If you need anything in the future, my door’s open.

Best,
[Your Name]

P.S. - Our Chief Architect is available anytime if you want to revisit the technical review.

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To VP Sales:
Subject: I’m out - but let me know if I can help

[VP Sales Name],

This is my last email. I know you’ve got a million priorities, and if this isn’t one of them, I totally get it.

If I misread the situation or if there’s something blocking this internally, any feedback would be helpful.

If things shift and this becomes a priority again, just reply “reconnect” and I’ll set up a call.

Good luck with the Q2 push.

Best,
[Your Name]

Why this works: Genuine break-up (not manipulative), feedback request, easy re-engagement option, respects their time

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Execution Calendar

Day	Date	Stakeholder	Channel	Message Summary	Status
1	[Today]	CFO	Email	ROI model, meeting request	Send
1	[Today]	CTO	Email	Technical addendum offer	Send
1	[Today]	VP Sales	Email	Productivity impact, blocker check	Send
3	[+2 days]	VP Sales	LinkedIn	Priority check, threading transparency	Remind
6	[+5 days]	All Three	Email (separate)	Role-specific value-add articles	Remind
9	[+8 days]	VP Sales	Phone	Direct voicemail with yes/no question	Remind
11	[+10 days]	All Three	Email (group CC)	Group accountability, 3 options	Remind
14	[+13 days]	All Three	Email (separate)	Individual break-up emails	Remind

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Response Handling Guidance

If CFO Responds First

• Schedule financial deep-dive, offer to bring your CFO
• Ask CFO to loop in CTO for technical sign-off

If CTO Responds First

• Provide technical addendum immediately, offer architecture review
• Once resolved, ask CTO to connect you with CFO for budget approval

If VP Sales Responds First

• Position VP Sales as internal champion
• Coach on navigating CFO (budget) and CTO (technical) approval

If Multiple Respond

• Coordinate joint call with all three stakeholders
• Move to contract negotiation with clear timeline

If No Response After Day 14

• Set 6-month reminder, move on to other opportunities

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Expected Outcomes:

• Best case (40%): One stakeholder responds by Day 6, deal advances
• Mid case (30%): Group email triggers response, evaluation extends
• Break-up response (20%): Day 14 break-up gets “yes, let’s reconnect”
• No response (10%): Deal is dead, follow up in 6 months