Selling SaaS to Buyers Who Don’t Know They Need It

Most bootstrapped SaaS founders aren’t losing to competitors. They’re losing to “we’ll deal with that later.” When your customer doesn’t feel urgent pain—or doesn’t even realize there’s a problem—marketing becomes a slow grind.

That’s why Episode 739 of Startups For the Rest of Us (Rob Walling with Andy Kim, co-owner of Rado) is worth studying. Rado sells “Go Links”—an internal URL shortener for companies. Retention is extremely high once a team adopts it, but the hard part is getting anyone to care before they’ve used it.

This post is part of the US Startup Marketing Without VC series, so we’re going to treat this episode like a case study: how do you create problem awareness and sell a product when your buyer isn’t looking for you yet—without a venture budget?

The real problem isn’t your SaaS—it’s customer awareness

If prospects aren’t searching for your category, you’re not doing “demand capture.” You’re doing demand creation. That changes everything: your channels, your messaging, your timeline, and your expectations.

Rob frames Rado’s challenge using Eugene Schwartz’s five stages of awareness:

1. Unaware (they don’t know the problem exists)
2. Problem-aware (they feel pain but don’t know solutions)
3. Solution-aware (they know solutions exist)
4. Product-aware (they know your product exists)
5. Most-aware (they’re ready; they just need the right offer)

Rado lives heavily in stages 1–2. Most people haven’t heard of Go Links, and even if they have the pain (lost links, duplicated resources, “where did Rob send that?”), they don’t label it as a category.

Here’s the stance I’ve found to be true across bootstrapped B2B: if your market is mostly unaware, your job is to name the problem in the customer’s language—not yours.

Rado’s case study: a “sticky” product with a cold-start problem

Rado is a SaaS tool that lets teams create internal short links that only work inside the company (think Bitly, but internal).

A few details from the episode matter for marketing strategy:

• Pricing model: about $3 per user (per-seat pricing)
• Business status: profitable, six figures in revenue
• Retention: customers stay for years; seat counts expand as companies hire
• Usage pattern: Andy notes 20–30% of users are power users (5+ times/day), while overall adoption can reach roughly 70% monthly active usage inside mature accounts

That usage profile is marketing gold if you can get in the door.

Why buyers don’t “feel” the pain until after adoption

Go Links is a classic “workflow glue” product. Before adoption, the pain is diffuse:

• Links are scattered across Slack, email, docs, tickets, and wikis
• People waste minutes repeatedly (“where’s the onboarding doc?”)
• Knowledge gets re-created instead of reused

But no one totals it up. No one opens a budget request titled “reduce link-finding time.” So the founder’s challenge becomes: make the invisible cost visible.

A practical playbook for selling to the problem-unaware (without VC)

If you’re building in the US and you don’t have VC money to brute-force awareness, you need a tighter approach than “run more ads.” Rado’s situation suggests a repeatable framework.

1) Start with “ex-users” and migrators (the fastest path to revenue)

Andy’s most promising segment isn’t “every company.” It’s people who used Go Links at companies like Google, Netflix, or other tech orgs—and miss it at their new job.

This segment is powerful because it collapses the awareness ladder:

• They’re already solution-aware or product-aware
• They can champion internally (“we had this before; it worked”)
• They often sit in engineering/IT/ops where tools get adopted

Bootstrapped move: build your ICP around migration patterns, not firmographics.

Concrete ways to do this:

• Target job histories in outbound lists (e.g., former employees of “Go Links-native” companies)
• Write landing pages and sales emails that explicitly speak to the “I miss this tool” moment
• Add onboarding that makes it easy to recreate what they had before

Snippet-worthy line: Your best customers often aren’t problem-aware—they’re “replacement-aware.”

2) Sell the “moment,” not the category

When a category is unfamiliar, category education is expensive. A bootstrapped founder should focus on trigger events—moments when the pain spikes.

For Go Links, triggers might be:

• Rapid hiring (new employees can’t find anything)
• Tool sprawl (Slack + Notion + Confluence + Jira + Google Drive)
• Reorgs and team merges (links and resources get duplicated)
• Security/compliance pushes (internal resources shouldn’t be shared publicly)

Bootstrapped move: build campaigns around those triggers:

• “Your team doubled this year—here’s how to prevent knowledge chaos.”
• “If Slack is your knowledge base, you’re paying a tax every day.”

This is how you create demand without spending like a VC-backed company.

3) Make ROI simple enough for a quick internal yes

When pain is fuzzy, ROI must be concrete.

A lightweight ROI model you can use (and that Rado-like products can credibly pitch):

• Assume 70% of employees use the tool monthly after adoption (Andy’s observed average).
• If each active user saves 2 minutes/day finding links and resources,
• In a 500-person company, that’s 350 users × 2 minutes/day = 700 minutes/day (~11.7 hours/day).

Even at a conservative loaded labor cost (say $60/hour), you’re looking at ~$700/day of time value. That doesn’t need to be perfect; it needs to be believable and easy to explain.

Bootstrapped move: ship an ROI calculator that fits on one screen and supports your outbound.

4) Use product-led proof where search demand is low

Rob points out a key tension: if there’s little search volume, SEO alone won’t carry acquisition. True. But you can still use content to create credibility and conversion lift.

Content that works in low-awareness markets:

• Internal case studies: “How a 2,000-person company standardized links”
• “Before/after” workflow breakdowns
• Migration guides (from homegrown tools or old internal systems)
• Security/compliance explainers (SOC 2, SSO, access controls)

Rado has SOC 2 Type II and SSO—those aren’t marketing fluff. They’re often the difference between “no” and “approved.”

Bootstrapped move: turn compliance and IT readiness into sales enablement content. Not blog filler.

5) Accept that you may not get a single “silver bullet” channel

Rob shares a hard-earned truth from growing Drip: sometimes growth is a portfolio, not a one-channel miracle. You might never find the one channel that drives 70% of trials.

If you’re bootstrapped, that’s annoying because you don’t have a big team. But it’s also survivable if you manage it intentionally.

A realistic “no VC” channel mix for problem-unaware SaaS:

• Targeted outbound (high intent segments)
• Partner channels (IT consultants, productivity ops communities)
• A handful of high-performing content pages (not hundreds)
• Product-led referrals inside orgs (power users invite others)
• Community visibility (podcasts, niche newsletters, founder networks)

Snippet-worthy line: In low-awareness markets, you don’t scale a channel—you stack small wins until the flywheel turns.

What to do when retention is high but pipeline is unpredictable

Andy describes the hardest part as uncertainty: you can do a lot of marketing work and get nothing back. That’s the bootstrapped reality, and it hits harder when your product is sticky but your funnel is inconsistent.

Here’s a pragmatic operating system for this stage.

Track leading indicators you can control

If revenue lags because deals take time, you need metrics that tell you whether you’re making progress before money shows up.

Examples:

• Number of ICP accounts added to outreach list weekly
• Reply rate from your “ex-user” segment
• Number of second calls booked (stronger than first calls)
• Time-to-first-value in onboarding
• Expansion rate inside accounts (power users → broader adoption)

Build “champion kits” to reduce internal friction

When one person loves your product but needs approval, you win by making them look good.

A champion kit can include:

• A 1-page rollout plan
• Security/compliance overview
• ROI summary with assumptions
• Internal announcement template for Slack/Teams
• “Top 10 Go Links to create first” playbook

This is especially effective for bootstrapped startups because it scales your sales effort without hiring.

People also ask: “How do you market SaaS when customers don’t know they have a problem?”

Answer: you don’t start by explaining your product. You start by naming the hidden cost, targeting trigger events, and finding segments who already believe.

In practice:

1. Focus on “replacement-aware” buyers first (they’ve used something like it)
2. Attach your messaging to moments of pain (hiring, tool sprawl, reorgs)
3. Make ROI easy to repeat inside a company
4. Create proof assets that reduce perceived risk (security, case studies)
5. Stack channels instead of waiting for a single breakout

Where this fits in “US Startup Marketing Without VC”

Bootstrapped marketing in 2026 looks less like big ad budgets and more like precision: tighter ICPs, sharper positioning, and systems that help champions sell internally. Rado is a clean example because it’s not selling hype—it’s selling a workflow improvement that spreads once it lands.

If you’re building a SaaS product where prospects don’t wake up searching for you, take this as permission to stop chasing vanity impressions. Put your energy into identifying believers, engineering “aha” moments, and turning retention into a growth engine.

What’s the “replacement-aware” segment in your market—the group that already knows the value, and just needs you to show up at the right time?