SaaS Sales for Startup Founders

2. Self-Service vs. Sales-Supported SaaS

The Decision Framework

Use this three-question decision tree to determine if you need a sales team:

Question 1: Is your CLTV high enough?

• CLTV < $1,000 → No sales team. Focus on frictionless self-service acquisition.
• CLTV ≥ $1,000 → Proceed to Question 2.

Question 2: Are your bigger customers struggling to convert?

• Segment trial accounts by size. If large accounts convert at the same rate as small ones → probably no sales team needed yet.
• If large accounts convert at a lower rate → sales can fix the friction. Proceed to Question 3.

Question 3: Is there complexity in the sales process for your bigger accounts?

• Complexity = multi-stage buying cycles, multiple stakeholders, security/integration concerns, competitors being evaluated simultaneously.
• Low complexity → still no sales team.
• High complexity → Build that sales team.

Optimizing Self-Service with a Hidden Sales Team

Even if you claim to have no salespeople, consider using a small sales team to:

• A/B test cohorts (sales-touched vs. self-service)
• Identify what salespeople do that self-service can't
• Use those insights to "fix the bug" in your onboarding, UI, and email sequences

Enterprise Self-Selection

Add a 4th "Contact Us" pricing tier with enterprise offerings (SSO, multi-seat, dedicated support). Large companies will self-select into it — and it signals to you when you have enough enterprise demand to justify a sales team.

3. Hiring and Paying SaaS Sales Reps

The Four Stages of Sales Hiring

Stage 1: Founder-Driven Sales (founders only) The founder must sell first. Even if you hate sales. Tap your network, do cold emails and calls, write a sales phone script. The goal at this stage is learning — not closing. You need to understand objections, pain points, and what messaging resonates.

Stage 2: Founder-Led Sales Team (2–3 sales reps) Hire 2–3 reps simultaneously (friendly competition, more data, more firepower). Stay deeply involved — you can't outsource this yet. Before moving on, achieve:

• Tested cold-email templates
• Effective lead management system
• Experience negotiating deals
• Predictability in your sales funnel

Stage 3: Junior Sales Leader (3–15 sales reps) Hire a sales manager or director who has scaled a small team to a larger one. They should fine-tune what you've built, grow the team, set quotas, and train reps.

Stage 4: Senior Sales Leader (25+ sales reps) Hire a VP of Sales — someone with a proven track record of scaling at the size you want to be. They'll build org structure, open new channels, and work on strategy.

Hire Hustlers, Not Sales Veterans

Good salespeople are never actively looking for sales jobs. Hiring experienced sales veterans as an early-stage startup is a trap — they need perks, infrastructure, and comp structures you can't offer.

Instead, look for hustler DNA:

• Self-driven and ambitious
• Entrepreneurial spirit
• High tolerance for rejection
• Competitive and coachable
• Genuinely enjoys communicating with people

Find them in your own network. Find founders of failed startups. Hire for attitude, not experience.

Commission Structure

Two valid approaches:

1. The collaborative way — Tell them upfront: "I don't know the right structure yet; let's figure it out together. Base salary for the first few months while we develop the plan."
2. The fake-it-till-you-make-it way — Present a structure based on the results you want. If reps can't hit it, let them go, reset, and hire new people with a more realistic structure.

Don't wait for the perfect commission structure. There's no such thing. Ship it, learn, iterate. Pay commissions upfront (e.g., at 3 months rather than spread over 12) to keep reps hungry.

4. Finding the Right B2B SaaS Customers

Create Your Ideal Customer Profile

1. List your 10 best current customers — Those who get the most value AND pay you the most.
2. Verify the value ratio — If they pay you $100/month, they should get at least $200 in value back.
3. Find common attributes — Industry, team size, job titles, tools used, buying process, how they found you.
4. Sell to them in three stages:
   • Before they buy — Sell the promise
   • After they buy — Sell implementation (get them to actually use it)
   • After they receive value — Sell the awareness of that value (make sure they know it was your product)

Lead Generation: Quality vs. Quantity Spectrum

Recommended: Find the core DNA of your 5 most successful customers — company size, employees, tools used, how they found you — and use that to generate a highly targeted list of similar companies.

Selling to Enterprise Customers

• Expect 6–18 month sales cycles
• Enterprise buyers want an account exec, not self-signup
• Price with a markup (they will negotiate down)
• Require pre-paid 1- or 2-year contracts
• Include a substantial onboarding/training package
• Develop an internal champion within the organization

Selling to Government (B2G)

Four stages (from SeamlessDocs' playbook):

1. Get buyer personas right — Map user buyers (IT), economic buyers (City Manager), and executive buyers (CIO/CTO). They're siloed and don't talk to each other.
2. Live on the phone — 90% of B2G demos come from cold calls, not email. Start with the IT user buyer; make them your champion.
3. Demo the problem, not the product — Start with: "How are you currently managing this process? What are the inefficiencies?" Get everyone to feel the pain before showing the solution. Sell efficiency, not innovation.
4. Midwife the procurement process — Know each government's procurement rules cold. Price strategically under spending thresholds to avoid vote/approval chains. Average B2G cycle: ~90 days.

5. Selling Like a SaaS Sales Pro

Handling Objection #1: "It's Too Expensive"

The pricing objection means you haven't communicated value yet. Never race to the bottom.

• Don't discuss price until value is established. If they ask too early: "What's your budget for this project? That'll impact how we structure the deal."
• Refuse to lower the price. Say: "This is the best deal we can offer." Lowering price tells them the product isn't worth what you said it was.
• Reframe from cost to cost-of-inaction. Ask: "What will it cost to keep doing what you're doing?"
• Do the math together. Calculate how many hours your product saves × their hourly cost. Make the ROI visible.

Handling Objection #2: "You're Missing a Feature"

Don't panic and promise to build it. Ask the engineer's question:

"We don't have that right now. Can you tell me why you need it, and exactly how you want to use it?"

Then either:

• Find a workaround using existing features
• Confirm it's a true dealbreaker (and be honest if it is)
• Offer to put it on the roadmap while being clear about timeline

Never overpromise. Trust is more valuable than a single close.

Charging for Things That Don't Exist Yet

Sell first, build second. If prospects want a feature you don't have, don't wait to build it before selling. Instead:

The Minimum Viable Pitch:

"It's clear that once we have this feature, we'll be the perfect solution for you. We plan to release it in [X months]. If you commit to a deposit today, you get a lifetime 50% discount and we'll prioritize the feature to ship in [X/2 months]. The deposit is fully refundable."

If you can't close 1 in 10 on this deal, your product/market fit may not be as strong as you think.

When Your Prospect Won't Switch Software

The #1 reason prospects don't switch: bad timing. They may have just gone through a 3-month vendor evaluation process.

Approach:

• Acknowledge it's not the right time
• Build a relationship over 6–18 months
• Follow up monthly or quarterly
• Be ready when their contract runs out or org changes

A long-pipeline prospect you're nurturing is a future customer being prepared.

Selling an Upfront Fee

Reframe the fee as being for the customer's benefit:

• A setup fee filters out uncommitted customers so you can serve the committed ones better
• It funds dedicated onboarding, training, and integration work
• Position it as part of an exclusive, top-tier service — not as a cost

"We only work with customers who are serious about success with us. This fee means we can pour resources into making you successful from day one."

Charge Early

Three reasons to charge users before you think you're "ready":

1. Real customers tell you what to build (fake interest doesn't)
2. Money gives you leverage and time
3. It filters out tire-kickers — only paying customers reveal what truly matters

6. Optimizing Demos and Trials

Running Product Demos That Sell

The key principle: don't demo features, demo solutions to their specific problems.

Before the demo:

• Research the company and the person
• Understand their pain points before you open the product

During the demo:

• Lead with questions: "What does success look like for you in 90 days?"
• Tailor the demo to show only what they care about
• Show the outcome, not the process
• Ask for feedback as you go — turn it into a dialogue

Close the demo with a direct ask.

Why Your SaaS Trials Are Too Long

Most trials are 30 days. They should be 14 days or fewer.

A shorter trial creates:

• Urgency
• Earlier activation
• Less "I'll look at this later" deferral

Match trial length to your activation event — how long does it realistically take a user to experience the core value? That's your trial length.

Call Every Trial Signup Within 5 Minutes

Calling a trial signup within 5 minutes of signup increases conversion dramatically. After 30 minutes, the odds of conversion drop by 100x.

The call doesn't need to be a sales call — it's a success call: "Hey, I saw you just signed up. I wanted to make sure you get the most out of the trial — what were you hoping to accomplish?"

Nursing Lost Trial Leads Back to Activation

Three approaches for users who signed up but never activated:

1. Direct outreach — Call or email asking what happened, offer to help
2. Drip email sequence — Targeted emails showing specific value based on what they signed up for
3. Time-based re-engagement — Reach out 30/60/90 days later; life circumstances change

7. Increasing Customer Lifetime Value

Happy ≠ Successful

The most important distinction in customer success: happy customers are not necessarily successful customers.

A happy customer is satisfied. A successful customer is achieving measurable business outcomes with your product.

Successful customers:

• Don't churn
• Expand their usage
• Refer others
• Give you testimonials

Focus your customer success efforts on making customers successful, not just satisfied.

Make Customers Actually Use What They Paid For

After a sale, sell implementation:

• Onboard them actively
• Set up a kickoff call
• Assign clear milestones
• Check in after 30 days

If they're not using the product, they will churn. Usage precedes renewal.

Visit Your Customers

Especially in the early days: visit your customers in person. You'll learn more in one afternoon than in 10 support tickets. You see their environment, meet the team, understand the workflow. This intelligence makes you a better product company and surfaces expansion opportunities.

Turn Outages into Opportunities

When something breaks:

1. Communicate immediately and proactively (don't wait for them to discover it)
2. Own the problem fully
3. Over-communicate the fix
4. Follow up after

How you handle failures builds more trust than how you handle successes.

How to Upsell

Upsell from a position of value already delivered:

• Identify customers who have hit usage limits or would benefit from more
• Frame the upsell as "you're getting so much value, there's more value available"
• Time it when they're experiencing success, not struggling
• Make the upgrade path frictionless

8. Losing (or Firing) B2B Customers the Right Way

Call Your Churning Customers

Before a customer churns (or after they've decided to), get them on the phone. Don't accept a cancellation form.

What to ask:

• "What's the main reason you're leaving?"
• "Was there a specific moment things went wrong?"
• "What would have needed to be true for you to stay?"

You won't save every churning customer — but you'll learn patterns. Those patterns fix future churn.

Even if you save 1 in 5, the revenue impact is massive. And if you can't save them, make the offboarding so good they refer you anyway.

When to Fire Your Customers

Some customers cost more than they're worth. Fire them when:

• They consistently abuse your support team
• Their use case is fundamentally incompatible with your product direction
• They're preventing you from serving your ideal customers
• The relationship is destructive to your team's morale

Fire them graciously. Help them find an alternative. Treat the offboarding like you'd want to be treated. How you handle exits shapes your reputation.

How to Use This Skill

When a user brings a sales question, first identify which phase of the sales lifecycle they're in:

• Pre-product / validation → Section 1: Validating Your SaaS Idea
• Self-service growing, unsure about sales team → Section 2: Self-Service vs. Sales-Supported
• Ready to hire → Section 3: Hiring and Paying Sales Reps
• Struggling to find customers → Section 4: Finding the Right B2B Customers
• In active sales conversations → Section 5: Selling Like a SaaS Sales Pro
• Trial/demo conversion problems → Section 6: Optimizing Demos and Trials
• Existing customers churning or not expanding → Sections 7–8: CLV and Churn

For each situation:

1. Diagnose the specific problem
2. Apply the relevant framework from above
3. Offer concrete language, scripts, or decision criteria — not abstract advice
4. Push back if the founder is avoiding the uncomfortable thing (e.g., charging money, making calls, firing bad customers)

The core recurring theme of this book: do the uncomfortable thing early. Call the prospect. Ask for money. Have the hard conversation. Founders who avoid discomfort in sales consistently lose to founders who embrace it.