Pricing as a journey: secret to scaling bootstrapped SaaS with Vova Feldman @Freemius

saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by https://saas.group/, a serial acquirer of B2B SaaS companies.

In episode #47 of season 5, Anna Nadeina talks with Vova, founder of Freemius, an all-in-one platform for payments, subscriptions, and taxes, helping you sell software globally while focusing on building great products.

I started Freemius because I was tired of seeing makers spend months on integrations, payments, taxes and company headaches instead of building the product. What began as a two-weekend technical prototype grew into a subscription business that was profitable from day one. The real lesson for me was simple: building the product is often the easy part. Turning it into a business is the hard part.

Origin story: from a side project to a business in a box

I was a technical founder and CTO for years. After my previous startup was acquired, I kept a little side project running. The user feedback and usage convinced me it could be more than a hobby. I partnered with someone, commercialized the product, and we started paying ourselves a salary. The core product barely changed — what changed was everything around it: payments, subscriptions, taxes, support and marketing.

That realization became the thesis for Freemius: reduce time to market from months to minutes for software makers. We started in WordPress because it was the largest, most fertile ecosystem for plugins and themes. Many of those projects were side hustles, exactly the audience we wanted to help.

Finding the first customers: build trust, one step at a time

As a “business in a box” platform, asking companies to put their business on an unproven platform is a big ask. Finding the first customer took about a year. We started with very small makers and gradually moved up as we built case studies, testimonials and migration support. Early customers require extra attention — if the fit is right, go the extra mile to make them successful. Their feedback is invaluable and often applies to many others.

Pricing evolved — treat it as a journey, not a number

Pricing was never a static decision for us. We initially priced based on marketplace analogies and later discovered that was the wrong comparison. Over 11 years we adjusted pricing a few times. The biggest shift came from three combined inputs: customer feedback, competitive landscape changes, and becoming a more mature company that could operate more efficiently.

Key elements of our latest pricing redesign:

• We decoupled the base platform from WordPress-specific features so customers can pick what they need.
• Our new base revenue share is 4.7%.
• If you want the full WordPress-tailored solution it is an additional 2.3%.
• We introduced growth pricing so customers can predict exactly what they will pay, and the rate decreases with scale. Once you cross 100k in revenue, the amount above that threshold is taken at 5%.

“Think about pricing not as a number or package. Think about it as a journey.”

Growth pricing solved two pains: the constant, time consuming negotiation dance with payment processors as you scale, and the uncertainty new makers face when trying to forecast how much they will pay. Pricing itself can be a meaningful differentiator and a form of marketing.

Practical pricing advice

• Map the buyer journey: design every step to lead your ICP to the plan you want them to buy.
• Use social proof and credibility cues: testimonials, badges, refund policies and case studies reduce perceived risk.
• Make pricing predictable and easy to calculate. Remove surprises when possible.

Community: narrow focus, real value, and the compounding network effect

People want to belong to something that matters to their day-to-day work. Generic Slack groups and Discord servers often fail without sustained intention. Our community works because:

• It is narrow and relevant. Our audience is software makers and product people who face the same problems daily.
• It provides immediate, real feedback loops for product decisions. Hundreds of makers give fast, high-quality feedback we could not get any other way.
• It creates real opportunities: partnerships, buyer and investor introductions and access to service providers who offer discounts to the community.
• We combine online conversations with physical meetups to strengthen relationships and create serendipity.

Communities need investment. Early on I hired a community lead and learned that time zones and execution matter. Once you reach critical mass, a core group of members will drive much of the activity, but you still need to be intentional about events, matchmaking and new activations.

“People want to belong to something.”

Hiring and building the team: hire senior, look for missionaries, test fit fast

Over a decade we made plenty of hiring mistakes. Today we prioritize senior, hands-on people who are autonomous and ship. A single senior hire can change the trajectory of a small company. Key hiring principles we follow:

• Start with an intro call to feel chemistry and alignment. In a small team it matters that it is pleasant to work together.
• Assess fit, not just skills. Ask where candidates see themselves in 3 to 5 years and whether the role supports their growth aspirations.
• Look for missionaries — people with passion and origin stories that show long-term commitment to their craft.
• Be willing to move quickly if it is not working. One month is often enough to know if a hire is the right fit.

Sample screening questions I use:

1. Why this role and why now?
2. Where do you want to be in 3 to 5 years?
3. What do you expect to get from this job that you didn’t have previously?

Expanding beyond WordPress: when and how to scale the market

We always planned to expand beyond WordPress, but timing matters. Rebranding and moving into broader SaaS, desktop apps and browser extensions required product and messaging changes. The product foundations were transferable, but experience, integrations and pricing needed rework.

Two important considerations when expanding:

• Be prepared to educate the new market. Change your language, conferences and outreach to match the new audience.
• Revisit pricing and modularity so customers can choose base platform features without paying for ecosystem-specific add-ons unless they need them.

AI: practical adoption and product implications

AI changed how we work internally and what customers need. Internally, AI helps with marketing productivity, test generation and repetitive developer tasks. Externally, AI forced a big shift toward usage-based pricing because AI products consume API tokens and incur variable costs.

How we manage AI adoption:

• Leadership experiments first. If something proves valuable, we roll it out to the team rather than forcing everyone to chase every new tool.
• Allocate time for experimentation. I personally spend an hour a week testing prompts and tools and keep a shared document of high-value prompts.
• Teach prompt framing: define the role and persona for the model, and specify the desired style and tone before asking for work. For example, “Write this OKR summary in the concise, emotional style of Steve Jobs.”

AI is powerful but noisy. Not every tool is worth the time; the signal-to-noise ratio can be low. Focus on what reduces real friction for your team and customers.

Biggest win and biggest lesson

Biggest win: the team. Moving from a founder-heavy operation to a team of senior, autonomous people completely changes what the company can achieve. Great people attract more great people, and that compounds.

Biggest lesson: beware of being too innovative for your market. A past example was rolling out advanced usage data collection for WordPress plugins. From a product perspective it was obvious and useful. From the ecosystem perspective it felt invasive to many users, and the backlash taught us to consider timing, norms and communication more carefully.

Founder hacks: time, stoicism and focus

• Start the day without your phone. Plan the day first and avoid getting dragged into reactive mode by notifications.
• Control your calendar. As founder, your most valuable job is setting priorities and moving the company forward, not just extinguishing fires.
• Cultivate calm. Stoicism helps: emotions are real, but reasoned decisions scale better than emotional responses in the long run.

Final thHow bootstrapped SaaS founders can scale sustainably — pricing as a journey, building trust, hiring right, and embracing AI. #SaaSUnboundoughts

Pricing, community, hiring and product expansion are all journeys. Treat pricing as a predictable, measurable path rather than a single number. Build a focused community that participates in your product journey. Hire senior, mission-led people and test fit quickly. Use AI where it saves real time and prepare your pricing for usage-based realities. Keep a calm, intentional founder mindset that protects your most valuable resource: time.

If you are building software, focus on removing friction for your customers so they can ship more and worry less about the surrounding business mechanics. That is the work that actually scales.