Talent Onboarding Guide #3
Your profile got you noticed. Your video introduction sparked interest. Now comes the moment of truth: the proposal.
This is where most experienced executives stumble. They're brilliant at strategy, operations, and leadership – but they've never had to write a sales document. They treat proposals like project plans instead of persuasion tools.
The result? Proposals that read like academic papers instead of compelling business cases. Technical specifications instead of transformation stories. Feature lists instead of value propositions.
But here's the thing: fractional clients aren't just buying your expertise. They're buying confidence that you can solve their specific problem better than anyone else. Your proposal needs to create that confidence while demonstrating exactly how you'll deliver results.
The proposal mindset: Selling transformation, not time
You're not bidding on a project
Project thinking: "Here's what I'll do and how much it costs."
Transformation thinking: "Here's the problem you're facing, why it matters, and how I'll solve it to create specific business outcomes."
You're solving a business problem, not completing tasks
Most job briefs focus on activities ("we need someone to improve our marketing"). Winning proposals reframe this as business outcomes ("you need to break through the growth plateau that's threatening your next funding round").
You're competing against alternatives, not other proposals
Your real competition isn't just other fractional leaders. It's:
- Hiring a full-time executive
- Using internal resources
- Working with an agency
- Doing nothing and hoping the problem resolves itself
Your proposal needs to position fractional leadership as the best solution to their specific situation.
The winning proposal structure
Opening: Demonstrate understanding (not just acknowledgment)
Weak opening: "Thank you for the opportunity to propose on your marketing leadership role."
Strong opening: "Based on your brief and market context, you're facing a classic Series A challenge: you've proven product-market fit with founder-led sales, but growth has plateaued at $2M ARR. The symptoms you're experiencing – inconsistent lead quality, lengthening sales cycles, and difficulty scaling the team – are exactly what I've helped six other B2B SaaS companies navigate in the past 18 months."
What this accomplishes:
- Shows you understand their specific situation
- Demonstrates relevant experience
- Positions their challenge as solvable (you've done it before)
- Creates confidence that you "get it"
Problem diagnosis: Show your expertise
Don't just repeat their problem statement. Provide insight into what's really happening and why.
Template: "While [surface problem] is the immediate concern, the underlying challenge is [root cause]. This typically happens when [business context] creates pressure on [specific business function]. Left unaddressed, this usually leads to [negative consequences], which explains why [specific symptoms they're experiencing]."
Example: "While inconsistent lead quality is the immediate concern, the underlying challenge is the transition from founder-led to systematic revenue generation. This typically happens when early product-market fit creates growth pressure that outpaces the informal systems that got you here. Left unaddressed, this usually leads to lengthening sales cycles and declining conversion rates, which explains why your CAC has increased 40% over the past six months."
Solution approach: Your unique methodology
This is where you differentiate yourself from other fractional leaders. Don't just list what you'll do – explain your approach and why it works.
Framework: Approach + Rationale + Differentiation
Example: "My approach centres on building systematic revenue generation rather than just optimising existing processes. Most marketing consultants focus on tactics – campaigns, channels, and messaging. I focus on building the engine: lead qualification systems, sales-marketing alignment processes, and predictable pipeline generation.
This works because sustainable growth requires systems that function independently of any individual. Rather than creating dependency on my ongoing involvement, I build capabilities that your team can maintain and scale.
What makes this different: I've been through this exact transition as a fractional CMO six times. I know which systems to implement first, which metrics actually predict growth, and how to avoid the common pitfalls that derail most scaling efforts."
Specific outcomes: What success looks like
Be specific about the results you'll deliver. Use ranges based on your experience, and tie outcomes to their business goals.
Template: "Based on similar engagements, you can expect:
- [Specific metric] improvement of [range] within [timeframe]
- [Business outcome] that typically results in [business impact]
- [Capability building] that enables [long-term benefit]"
Example: "Based on similar engagements, you can expect:
- 40-60% improvement in lead quality (MQL to SQL conversion) within 90 days
- Predictable pipeline generation that supports your $5M ARR target by end of year
- Marketing and sales alignment processes that eliminate the handoff issues currently causing 30% of leads to go unworked
- A marketing team that can operate systematically without founder involvement, preparing you for Series B fundraising"
Implementation plan: How you'll deliver
Show your structured approach without getting bogged down in unnecessary detail. Focus on phases and milestones that align with their business priorities.
Phase structure template: "Phase 1 (Weeks 1-4): Diagnosis and Quick Wins
- [Specific activities that provide immediate value]
- [Early results they can expect]
Phase 2 (Weeks 5-12): System Building
- [Core systems and processes you'll implement]
- [Capabilities you'll build in their team]
Phase 3 (Weeks 13-20): Optimisation and Scaling
- [How you'll refine and scale what's working]
- [Transition planning for ongoing success]"
Working relationship: How you operate
Address the practical aspects of working together. This builds confidence and sets appropriate expectations.
Cover:
- Time commitment and availability
- Communication preferences and cadence
- How you integrate with their team
- What you need from them to be successful
Example: "I work most effectively as an embedded partner rather than an external consultant. My typical approach:
- 2-3 days per week, with flexibility around key meetings and deadlines
- Weekly 90-minute strategy sessions plus ongoing Slack communication
- Direct collaboration with your sales team and key stakeholders
- Monthly progress reviews against agreed metrics
For this to work best, I'll need: access to your current marketing and sales data, regular feedback from your sales team, and authority to implement changes within the agreed scope."
Investment and terms: Value, not just cost
Position your fees in the context of the value you'll create and the cost of not solving the problem.
Framework: Context + Investment + Value
Example: "The cost of not solving this growth plateau extends beyond missed revenue – it impacts your ability to raise Series B and could force you to consider more dilutive funding options.
My investment for this engagement: $15,000 per month for 6 months ($90,000 total), structured as a monthly retainer that includes all strategy, implementation, and team development work.
Context: This is approximately 40% of what a full-time CMO would cost (including equity and benefits), while delivering the specialised expertise and focused execution that typically takes internal hires 12-18 months to develop."
Proposal personalisation strategies
Reference their specific context
Use details from their brief:
- Company stage and recent milestones
- Specific metrics or challenges mentioned
- Industry or market context
- Team size and structure
Example references:
- "Given your recent Series A and 18-month runway..."
- "With your expansion into enterprise customers..."
- "As you prepare for international market entry..."
Connect to their business goals
Link your work to their bigger picture:
- Funding milestones
- Revenue targets
- Market opportunities
- Competitive pressures
Example: "This marketing engine directly supports your goal of reaching $10M ARR by the end of year, which positions you perfectly for Series B fundraising in Q2 next year."
Address their specific concerns
If they mentioned:
- Previous bad experiences with consultants
- Budget constraints
- Timeline pressures
- Team capacity issues
Address it directly: "I understand you've had disappointing experiences with marketing agencies that over-promised and under-delivered. My approach is different: I embed with your team, take accountability for results, and build capabilities that outlast my engagement."
Common proposal mistakes
Leading with credentials instead of value
- The mistake: Starting with your background and experience.
- Why it fails: They've already seen your profile. The proposal should focus on solving their problem.
- Better approach: Start with their situation and how you'll address it.
Being vague about outcomes
- The mistake: Promising to "improve performance" or "drive growth" without specifics.
- Why it fails: Doesn't give clients confidence in your ability to deliver measurable results.
- Better approach: Provide specific outcome ranges based on your experience.
Focusing on activities instead of results
- The mistake: Detailed lists of what you'll do rather than what you'll achieve.
- Why it fails: Clients buy outcomes, not activities.
- Better approach: Lead with results, support with methodology.
Competing on price instead of value
- The mistake: Positioning yourself as the affordable option.
- Why it fails: Fractional clients are paying for expertise, not seeking the cheapest option.
- Better approach: Justify your investment with the value you'll create.
Generic proposals that could work for anyone
- The mistake: Template proposals that don't reference their specific situation.
- Why it fails: Doesn't demonstrate understanding of their unique challenges.
- Better approach: Customise every proposal to their specific context and needs.
Handling common objections
"Your rate seems high compared to other proposals"
- Response approach: Reframe around value and ROI, not hourly cost.
- Example: "I understand cost is important. Let me put this in context: the difference between my proposal and a lower-cost option is about $3,000 per month. But if my approach delivers even 10% better results – say an extra $200K ARR by year-end – that's a 6x return on the additional investment. Given that I've delivered 40-60% improvements in similar situations, the ROI potential is significant."
"We need someone to start immediately"
- Response approach: Acknowledge urgency while setting realistic expectations.
- Example: "I appreciate the urgency, and I can start within two weeks. However, rushing the foundation work would compromise the results. My first 30 days focus on quick wins while building the systems that drive long-term success. You'll see meaningful progress within the first month, but sustainable transformation takes 90-120 days."
"We're not sure about the time commitment"
- Response approach: Show flexibility while maintaining effectiveness.
- Example: "I'm flexible on structure, but effectiveness requires minimum investment. I could start with 2 days per week for the first month while we calibrate the right level of engagement. Most clients find that consistent involvement delivers better results than sporadic intensive periods."
"We might want to hire full-time instead"
- Response approach: Position fractional as a strategic stepping stone.
- Example: "That's a smart long-term strategy. Fractional work actually helps with full-time hiring – I'll help define the exact role requirements, build the foundation systems, and can assist with recruiting when you're ready. Many clients use fractional leadership to prove the ROI before committing to full-time investment."
Follow-up and negotiation
Proposal submission best practices
- Timeline: Submit within 24-48 hours of receiving the brief
- Format: PDF with clear structure and professional formatting
- Follow-up: Email confirming receipt and offering to answer questions
Questions that close deals
After submitting your proposal:
- "What questions does this raise about the approach?"
- "How does this align with your timeline and expectations?"
- "What would need to be different for this to be perfect for your situation?"
Negotiation principles
Where to be flexible:
- Start date and timeline
- Specific deliverables and milestones
- Time commitment structure
- Payment terms
Where to hold firm:
- Overall scope and outcomes
- Quality standards
- Core methodology
- Monthly retainer amount (you can adjust structure, not value)
Universal proposal template
Use this template for any fractional role – customise the specifics:
1. Opening: Demonstrate understanding
"Based on your brief and [company context], you're facing [specific challenge type]. The symptoms you're experiencing – [specific issues mentioned] – are exactly what I've helped [number] other [company type] navigate in the past [timeframe]."
2. Problem diagnosis: Show your expertise
"While [surface problem] is the immediate concern, the underlying challenge is [root cause]. This typically happens when [business context] creates pressure on [specific area]. Left unaddressed, this usually leads to [consequences], which explains why [their specific symptoms]."
3. Solution approach: Your unique methodology
"My approach centers on [your core methodology] rather than just [what others typically do]. This works because [rationale]. What makes this different: [your unique differentiator based on experience]."
4. Specific outcomes: What success looks like
"Based on similar engagements, you can expect:
- [Specific metric] improvement of [range] within [timeframe]
- [Business outcome] that typically results in [business impact]
- [Capability building] that enables [long-term benefit]"
5. Implementation plan using Shepherd's SOW structure
"My proposed approach follows this structure:
Engagement Overview [Brief description of role, primary responsibilities, and key challenges/opportunities you'll address]
Objectives and Key Results (OKRs) 1. Objective: [Primary Objective relevant to their brief]
- KR1: [Measurable Key Result]
- KR2: [Measurable Key Result]
- KR3: [Measurable Key Result]
2. Objective: [Secondary Objective]
- KR1: [Measurable Key Result]
- KR2: [Measurable Key Result]
Checkpoints and Deliverables
- [30-day milestone] - Quick wins and assessment complete
- [60-day milestone] - Core systems/processes implemented
- [90-day milestone] - Results measurable and scaling initiated
Success Metrics
- [Specific KPI tied to their business goals]
- [Specific KPI tied to their business goals]
- [Specific KPI tied to their business goals]"
6. Working relationship: How you operate
"I work most effectively as [your approach]. My typical structure:
- [X] days per week, with flexibility around key meetings and deadlines
- [Communication preferences and cadence]
- [How you integrate with their team]
- [What you need from them to be successful]"
7. Investment and terms: Value, not just cost
"My investment for this engagement: $[amount] per month for [duration] ($[total] total), structured as a monthly retainer.
Context: This represents approximately [percentage] of what a full-time [role] would cost, while delivering the specialised expertise and focused execution that typically takes internal hires [timeframe] to develop."
Your proposal checklist
Content strategy:
- [ ] Demonstrated understanding of their specific situation
- [ ] Diagnosed root cause, not just surface symptoms
- [ ] Explained your unique approach and methodology
- [ ] Provided specific outcome expectations with ranges
- [ ] Outlined clear implementation phases and milestones
- [ ] Addressed practical working relationship details
Persuasion elements:
- [ ] Referenced their business context and goals
- [ ] Connected your work to their bigger picture
- [ ] Positioned investment in context of value created
- [ ] Differentiated from alternative solutions
- [ ] Built confidence through relevant experience
- [ ] Addressed potential concerns proactively
Professional presentation:
- [ ] Clear structure and professional formatting
- [ ] Specific to their situation, not generic template
- [ ] Appropriate length (2-4 pages typically)
- [ ] Error-free writing and presentation
- [ ] PDF format for easy sharing and printing
Follow-up preparation:
- [ ] Ready to answer questions and provide clarification
- [ ] Prepared for common objections and negotiations
- [ ] Clear on timeline for their decision-making
- [ ] Follow-up sequence planned for staying engaged
The compound effect of great proposals
Every proposal you write makes you better at the next one. You'll start to recognise patterns in client challenges, refine your methodology explanations, and develop stronger value propositions.
But more importantly, great proposals that win work create:
- Case studies for future proposals
- References that validate your approach
- Refined methodologies that become your competitive advantage
- Confidence in your ability to win premium engagements
The bottom line
Your proposal isn't just a response to their brief – it's a demonstration of how you think, solve problems, and create value. Clients are evaluating not just whether you can do the work, but whether you can think strategically about their business.
The best fractional leaders treat proposal writing as a core business skill. They invest time in understanding client psychology, refining their value propositions, and developing repeatable frameworks that win work consistently.
Remember: you're not just competing for this project. You're building the reputation and skills that will win you premium fractional work for years to come.
Next up: Your first 90 days - proving value as a fractional leader. Learn how to start strong, build relationships, and establish yourself as indispensable to your new client.
