Founder-led Sales : Strategy and Guide (with AI Prompts) - Part 1 of 3
Discover actionable, founder-led sales strategies designed for solopreneurs and startup founders. Learn to craft compelling narratives, optimize outreach, and master GTM strategies with examples.
I came up with the idea for this newsletter during one of those long, quiet evenings. I was reflecting on my journey of building businesses and the hard-won lessons I learned along the way.
I was wrapping up another day of brainstorming calls. I noticed recurring questions and challenges related to “founder-led sales” in every conversation. I remembered the early days of cold calls and endless follow-ups. I recalled how I turned each “no” into a learning moment. I saw a pattern—my struggles, successes, and tweaks could be a roadmap for fellow founders and business / sales leaders.
I wanted to create a simple guide to help founders and leaders build trust and generate revenue. I decided to write this newsletter to share my journey in a way that’s simple and relatable. I want every founder to know that success comes from constant learning and refining.
I have divided this guide into a 2 part series.
I am going to cover the following topics below…
1/ What's founder-led sales? What's my personal story?
2/ How have I started with Founder Led Sales? What have been ups and downs?
3/ How do I plan work items when launch a new initiative as a founder? And How does work items evolve over time?
In the next part, we will cover the following topics.
4/ How Is AI Enabling Your Work Items in Founder Led Sales?
5/ What’s Your “Founder-led Sales” Playbook?
What's founder-led sales? What's my personal startup story?
Founder-led sales is a hands-on, personal way to bring in revenue.
I had an interesting experience in the last 7 years. I jumped into the dirt. I got my hands dirty and mapped what people really needed. I learned sales and marketing by doing it myself.
I started with ReFier -- onboarded 54 trainers, helped over 10,000 learners, worked with 12 companies over a span of 13 months. I was in every sales conversation and listened diligently. I asked, "What do you need?" This simple approach built trust.
With ReFier 2.0, I leveled up my approach -- partnered with 21 companies, placed more than 300 folks after sales training, learned to pivot when the market changed in just 8 months.
Then pivoted to Recruitment Stack. I reached out to more than 120 recruitment agencies in just 3 months… did pilots with 42 recruitment agencies and validated revenue. I learned that a clear, focused message always works.
At StartupGTM, I talked to over 150 founders and shared ideas on go-to-market strategies and started writing this newsletter which has impacted more than 5000 founders, marketing and GTM professionals.
For Whatlist, I spoke with over 300 founders and business leaders in 10 months. I dove deep into their challenges with WhatsApp workflows. I mapped out solutions that fit their needs.
Here’s what I learned along the way in founder-led sales strategy:
- Be personal: When you talk directly to people, they trust you.
- Be in the dirt: Get involved. Understand the problems deep and close.
- Map their needs: Listen carefully and adapt your pitch.
I know some say that founder-led sales is too time-consuming. They think you should leave sales to the sales team. But I disagree. Being the founder means you know the story best. Your personal touch makes all the difference.
There is always room to do better. I sometimes wished I had better tools to track every conversation. I learned the hard way that data matters. Still, every meeting, every call, built my credibility.
"Startup Founder as the first sales person" Model:
The “Founder as the First Salesperson” model is a simple yet powerful idea. It says that the founder should be the one to start selling. Your voice carries weight. Your story is real. Your expertise is deep. Here is a framework that would help you:
1. Build Personal Credibility.
Be visible. Your face and story matter. Show your passion. Speak from the heart.
Example: I shared my journey on LinkedIn. I explained my early stage struggles and wins. People trusted my words.
KPI: Track the conversion rate from founder-led outreach.
Tip: Always ask for feedback. Some meetings may need more follow-up.
2. Leverage Deep Domain Expertise.
Know your stuff. Your knowledge sets you apart.
Be a teacher. Share tips and tricks from your own playbook.
Example: I broke down complex ideas into simple tips for startup founders. They could see I understood their problems.
3. Use Authentic Storytelling.
Tell your story. Use short, vivid sentences.
Make it real. Share both wins and struggles.
Example: I told the story of onboarding 54 trainers at ReFier. I shared the hard lessons learned along the way.
4. Combine the Three for Early Revenue.
Step 1: Introduce yourself and your mission.
Step 2: Share a quick success story.
Step 3: Explain how you solve a real problem.
Step 4: Invite them to a quick chat or demo.
Process Tip: Write a short script. Test it. Refine it.
This method works best when you stay true to yourself and learn from every interaction.
Personal Narrative AI Prompt Template
(I have updated it with my details.. you can edit and update with your details)
"Write a personal narrative that blends my founder-led sales journey with key metrics and customer wins. Use a conversational tone and short, simple sentences. Evoke authenticity and trust by sharing real challenges and victories. Include the following details:
- Introduction:
- Introduce me as a founder who has built multiple businesses and scaled them to high ARR
- State my passion for industry and skills - sales, marketing, and growth.
- Emphasize how i learned this unique POV - doing sales by getting in the dirt and talking directly to people.
- Key Metrics & Wins:
[
- Mention onboarding 54 trainers at ReFier and delivering online training to 10K+ learners and 12 companies.
- Highlight partnering with 21 companies at ReFier 2.0 and placing 300+ individuals post-training.
- Include the win of onboarding 42 recruitment agencies in 3 months for Recruitment Stack.
- Note the achievement of advising 150+ founders through StartupGTM.
- Mention talking to 300+ founders and business leaders via Whatlist to solve real business challenges.]
- Storytelling Elements:
[ - Describe the early days of cold outreach and the personal touch in each conversation.
- Share a brief anecdote about a challenging moment that turned into a win.
- Use bullet points to outline key steps taken: initial contact, follow-ups, learning from feedback.
- Emphasize the importance of authenticity and deep domain expertise.]
- Closing & Impact:
[ - Conclude with how these experiences built my credibility and trust.
- Mention how every conversation taught me something new and fueled further growth.
- End with a statement on how mapping others' needs turned cold outreach into loyal customer relationships.]
Ensure the narrative is vivid, engaging, and easy to read. Use clear, simple language, and include metaphors or figurative language when it makes ideas more memorable. The story should feel like a real conversation with a trusted friend, honest and direct."This template can be used with any AI tool to generate a narrative that is both personal and data-driven, evoking a strong sense of authenticity and success.
Resources & Pitfalls:
Here are some great resources on founder-led sales storytelling and a few pitfalls to watch out for.
- Founder Led Sales by Pete Kazangy.
- Articles by Jan Abel on Medium.
- Blog posts by Alex Kracov.
How have I started with founder-led sales strategy ? What have been Ups and Downs?
Here’s a detailed timeline of my journey in founder-led sales, starting from necessity and moving through ups and downs.
Early Days – Necessity Drives Action.
- I bootstrapped my startup. I had to wear many hats and stepped in to lead marketing and sales since we needed revenue fast.
- I asked myself, "What can I offer for free to get a meeting?". I learned by talking directly to prospects.
ReFier 1.0 – Building a Training Platform.
I launched ReFier as a training platform for non-tech roles.
We faced one big challenge: COVID hit and took our major B2B revenues away and had to pivot from B2B to B2C quickly.
Key questions I asked:
- "What do my prospects really need right now?"
- "How can I adapt my offer to fit a changing market?"
I learned that a quick pivot can save a business.
ReFier 2.0 – Training-Led Hiring.
I re-launched ReFier 2.0 focused on training led hiring for sales roles and built credibility by writing newsletters focused for CHROs.
I optimized my time by splitting activities between lead generation, sales calls, and follow-ups and constantly asked, "Is my goal problem validation, solution validation, or revenue validation?”
Recruitment Stack – A New Challenge in 2022.
In 2022, interest rates dropped the funding cycle for startups.
This reduced the need for hiring and hit our training-led hiring model hard.
We pivoted to Recruitment Stack – a SaaS plus marketplace for recruitment agencies and onboarded 42 recruitment agencies in just three months.
I asked, "How can I offer something valuable for free to get a meeting?” and refined my sales pitch and built trust by mapping out clear solutions.
Challenges and Pivoting.
Demand in hiring kept falling.
I had to decide when to stop sales efforts for Recruitment Stack.
I learned that sometimes, knowing when to pivot is as important as knowing when to push forward.
StartupGTM – Sharing the Learnings.
I began StartupGTM to help founders with go-to-market strategies. I talked to over 150 founders and shared my journey, failures, and wins in this newsletter with 1,100+ subscribers.
I answered questions like:
- "What do I know that others need to learn?"
- "How do I build credibility in real time?"
- I turned my lessons into advice that others could use..
How do I plan work items when launching a new initiative as a founder? And How do work items evolve over time?
When launching a new initiative, the go-to-market (GTM) plan is your blueprint. It starts with validation, gets refined, and scales with experimentation.
Here's how to do it step by step.
1. Problem-Solution Validation (Target: 30 Interactions)
Before selling anything, confirm that the problem you’re solving is real and painful.
Step 1: Craft Your Story Narrative
- Why this problem? Why now?
- Do you have real experience that makes you the right person to solve it?
- Frame your narrative in a way that speaks to your audience’s frustrations.
✅ Example: When I launched ReFier, I saw that companies struggled to train sales teams. I framed my outreach with:
"Most founders struggle with hiring sales talent who ramp up fast. We built a structured training-led hiring model that delivers pre-trained sales reps. Would this help you?"
Step 2: Select Your Target Segment
- Resist the temptation to sell to everyone.
- Identify 2-3 key customer segments with the most urgent need.
- Run parallel validation efforts across segments to see who gets interested fast and take action.
Example: When I pivoted ReFier from B2B to B2C, I ran two tests:
1. Targeted HR heads at mid-sized companies.
2. Targeted individual job seekers looking for sales or other non-tech roles.
Step 3: Build Essential Collaterals
Must-haves:
LinkedIn connection message → Follow-up → Meeting booking flow.
Short email sequences (3-5 messages).
Concept deck (a 5-slide mini pitch on the problem + how you solve it).
Optional:
Marketing copy or ad copy to test messaging.
Whitepaper, blog, or newsletter to establish credibility.
Example: At Recruitment Stack, I tested two cold email versions. One focused on automation benefits, the other on cost savings. The cost savings sales pitch got 3X more replies.
Step 4: Distribution – Get in Front of Potential Customers
Pick 1-2 channels.
Options:
Tap into your network for warm intros.
Run a small LinkedIn ad experiment ($200-$500).
Direct cold outreach (email & LinkedIn).
✅ Example: For Whatlist, I started by manually reaching out to founders, industry professionals and community builders from the network. This helped me refine the pitch before automating lead generation through Ads..
2. Revenue Validation (Target: 5 B2B or 25 B2C Conversions)
Once people show interest, you need to convert them into paying customers. Whether it's b2b sales or b2c sales, just get in and start selling.
Step 5: Experiment and Iterate
Test different narratives. Does emphasizing “speed” work better than “cost”?
Refine pricing and trial models. What gets prospects to commit?
Optimize the onboarding experience for your product or service. How easy is it for them to say “yes”?
Does it require additional product development ? How easy it is for them to have the right product knowledge for gratification?
✅ Example: At StartupGTM, I started with free advisory calls.
- After 10 calls, I realized that people valued my frameworks the most.
- I productized my knowledge into a newsletter
Tip: If your close rate is below 10%, tweak your offer.
3. Evolving Work Items Over Time
Once validation is done, your GTM strategy needs to scale up.
Phase 1: Refining Outreach & Targeting
Move from broad outreach to focused geographies, company size, and job roles.
Use data from early sales to refine who your best customers are.
Phase 2: Expanding Collaterals
Start with a simple landing page and pitch deck → Expand into website, case studies, whitepapers.
Build real-world proof (testimonials, user-generated content).
Phase 3: Thought Leadership & Demand Generation
Shift from one-on-one sales to one-to-many (newsletters, LinkedIn posts, webinars).
Invest in content that positions you as an authority.
Phase 4: Systemizing Sales
From manual outreach → to repeatable inbound & outbound channels.
Invest in structured pricing, demos, and trial experiences.
All that is required to build final trust and close deals - A structured narrative, FAQs, Legal, Security, NDA and other agreements.
Example: At Whatlist, I went from manual outreach → to founders recommending it organically → to setting up automated workflows to nurture leads.
Final Takeaways
- Start small. Talk to 30 real people before automating anything.
- Nail your messaging first. If people don’t get it, they won’t buy.
- Iterate fast. If it’s not converting, change the pitch.
- Once validated, scale up. Move from founder-led sales to systemized sales.
The key? Be obsessed with learning. Every no, every pivot, every tweak gets you closer to a repeatable revenue machine.
Validation Pyramid of founder-led sales process
The Validation Pyramid is like a funnel that starts wide and then narrows down. It helps you test big ideas and then focus on what actually makes money.
Top of the Pyramid – Broad Hypothesis Testing.
Test the problem and solution with many people.
Talk to at least 30 prospects.
Ask simple questions like, "Does this problem hurt you?" and "Would my solution help?"
KPIs:
Number of Interactions.
Quality of initial feedback.
Example: I once reached out to 40 people with a new training idea. I learned quickly if the pain was real.
Middle of the Pyramid – Narrowing the Focus.
Filter out what works.
Look at conversion rates from interest to meetings.
Ask, "How many people want to learn more?"
KPIs:
Meeting booking rates.
Engagement levels during demos.
Bottom of the Pyramid – Revenue Validation.
Only then, focus on real revenue.
Aim for at least 5 B2B or 25 B2C conversions.
Ask, "Are people willing to pay?"
KPIs:
Conversion rates from demo to paying customer.
Revenue milestones.
Customer feedback scores on value.
My Opinion:
- Some say focus on revenue from the start. I disagree.
- You need to prove the problem exists before chasing money.
- This pyramid keeps you grounded and data-driven.
AI Prompts:
1. Prompt for Narrative Crafting
Draft a compelling story narrative that explains why we are solving this problem, including personal experience and market data.
Modifiers:
- Use a conversational tone.
- Include vivid, personal anecdotes.
- Support the narrative with specific market data points.
- Highlight key challenges and successes.
Context:
- Explain the background of the problem.
- Mention any critical market trends or data that validate the issue.
- Connect your personal journey and experience to the solution.
Breakdown:
- Introduction: Start with a hook that grabs attention.
- Example: "I remember the day I realized sales was more than just numbers—it was about real people and real struggles."
- Personal Experience: Describe your own encounters with the problem.
- Detail a specific moment where you faced a challenge.
- Market Data: Insert data points that show the scale or impact of the problem.
- Example: "Recent studies show that over 60% of startups struggle to convert initial interest into revenue."
- Solution Connection: Tie your personal experience and the data together to explain why your solution matters.
- Conclude with a call to action or an inspiring note.2. Prompt for Segment Validation
List potential target segments with key characteristics and validation questions based on this [idea].
Modifiers:
- Use clear, bullet-point formatting.
- Break down each segment into distinct, measurable characteristics.
- Include targeted questions that reveal pain points and needs.
Context:
- Explain why identifying the right segment is crucial.
- Consider industry, company size, job roles, or geographic location.
- Reflect on previous interactions or data that suggest certain segments are more promising.
Breakdown:
- Segment Identification: List each potential target segment.
- Example: "Small-to-medium-sized tech startups; Enterprise-level B2B companies; Freelance professionals in marketing."
- Key Characteristics: For each segment, note down specifics like:
- Industry focus.
- Size (e.g., employee count, revenue range).
- Typical challenges they face.
- Validation Questions: Write 3-5 questions for each segment.
- Example for tech startups:
- "What are your current sales challenges? Is it enterprise Sales or SMB Sales?"
- "How do you currently manage lead generation?"
- "What would be your top priority when investing in sales solutions?"3. Prompt for Collateral Creation
Produce a checklist of collaterals required for initial outreach (LinkedIn message, email sequence, concept deck, etc.).
Modifiers:
- Organize the checklist in a clear, bullet-point format.
- Specify the purpose of each collateral piece.
- Include creative ideas for personalization and design.
Context:
- Explain how these materials serve as the first impression.
- Consider what a prospect needs to understand quickly about your offering.
- Reflect on the need for both digital and print materials where applicable.
Breakdown:
- LinkedIn Message:
-- Purpose: To introduce yourself and spark interest.
-- Details:
--- Personal greeting.
--- One-liner on the problem you solve.
--- Call-to-action (CTA) to connect or schedule a call.
- Email Sequence:
-- Purpose: To nurture the lead.
-- Details:
--- First email: Introduction and pain point identification.
--- Follow-up emails: More details on benefits and social proof.
--- Final email: Urgency or special offer to book a meeting.
- Concept Deck:
-- Purpose: To provide a visual overview of your solution.
-- Details:
--- 5-7 slides outlining the problem, solution, market data, and testimonials.
-- Additional Materials (Optional):
--- Blog post or whitepaper that dives deeper into the problem.
--- Short video demo or customer testimonial clip.Loved this post?
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