Overview of SaaS Podcast: Founder-Led Sales: He Learned to Sell SaaS and Closed 50 Customers
This episode features Shahar Azule, co-founder and CEO of GroundCover, an observability platform competing with Datadog, New Relic, and Grafana. Shahar explains how he went from technical founder to hands-on seller, closed the company’s first customer with almost no product UI, and built the business to roughly $20M ARR, 250 customers, and 150 employees. A major theme is how GroundCover used eBPF and a bring-your-own-cloud architecture to break free from usage-based pricing and turn observability into a more scalable, customer-friendly product.
What GroundCover Does
GroundCover is an observability platform for engineering and DevOps teams. It helps customers monitor:
- Logs
- Metrics
- Traces
- Infrastructure and application behavior in production
Key differentiator
Instead of a traditional SaaS model where customers pay based on telemetry volume, GroundCover:
- Runs the data plane in the customer’s cloud
- Charges based on infrastructure size / host count
- Uses eBPF to collect high-fidelity telemetry without heavy code instrumentation
Shahar’s argument is that modern cloud and AI-era systems generate too much telemetry for legacy pricing models to make sense.
The Founder-Led Sales Journey
Shahar and his co-founder came from engineering/security backgrounds, not sales. Early on, they sold the product themselves and learned by doing.
First customer and first deal
- Their first customer came from their network in Tel Aviv: Lemonade
- The product had no UI at the time
- Shahar originally pitched $100K
- The deal closed at $10K
He frames that as an important lesson: in the earliest days, founders should focus less on perfect pricing and more on getting the first customers in the door.
Early sales motion
Their initial motion was highly founder-led:
- Heavy use of personal network
- LinkedIn outreach
- Direct demos from the CEO/founder
- A bit of product-led discovery via Product Hunt and early signups
Shahar estimates it took about 50 customers to reach the first $1M ARR.
How They Learned to Sell
Shahar says he was essentially doing:
- SDR work
- AE work
- Sales engineering
- Demoing
- POC support
all at once for a long time.
Why he stayed so involved
He didn’t step away quickly because:
- Technical sales was hard to hire for early
- He didn’t yet know how to train the role properly
- He could explain the product best
- Founder involvement helped shape product direction and sales messaging
Even after hiring sales leaders, he was still doing demos and sales work in other regions for years.
From Complement to Replacement
At first, customers saw GroundCover as a supplement to existing observability tools, not a replacement.
The shift happened gradually:
- Early customers used it for specific edge cases Datadog couldn’t cover
- Customers began asking GroundCover to help rip out Datadog
- The team realized they needed a real migration / displacement motion
- By around late 2024 into 2025, GroundCover’s parity and positioning made full replacement conversations much more common
What changed
- The messaging became clearer
- The product became more mature
- ACVs increased
- The company started winning bake-offs against incumbents
- Pricing and comp plans shifted to support replacement deals
Sales Lessons Shahar Emphasized
1. Close the first deals at any price
His view is that founders should prioritize learning and momentum early, even if the ACV is low.
2. Don’t over-focus on perfect pricing too early
Early-stage sales is about:
- Understanding customer pain
- Learning procurement
- Building confidence
- Gathering logos and references
3. Founder depth matters
His advice: be as deep in the business as needed, even if that means acting like an SDR or AE.
4. Market timing and confidence matter
A big unlock was when the team had enough confidence to say:
- “We can replace Datadog”
- “We can support migration”
- “We can win full displacement deals”
Go-To-Market and Company-Building Takeaways
What worked well
- Founder-led selling
- LinkedIn + network outreach
- Public pricing
- Field marketing and events
- Moving the U.S. team into offices
What didn’t work as well
- Hiring SDRs or AEs too early without enough operating momentum
- Assuming new sales hires could create demand in a vacuum
- Treating the first version of the product like a fully mature sales motion
Notable Advice and Insights
- “Closing at any price is what founders should do” in the first dozen opportunities.
- A CEO should be involved wherever the company is weakest or most important.
- Events can work very well, especially when the company is early and trying to build brand.
- In displacement sales, timing matters: sometimes you should move on rather than force a deal that doesn’t yet see you as a replacement.
Lightning Round Highlights
Best business advice
Be deeply involved in the areas that matter most; don’t over-index on what a CEO “should” or “shouldn’t” do.
Favorite book
The Hard Thing About Hard Things — because it reminds founders they’re not alone.
Best money spent
- Field marketing / events
- Office culture and in-person work in the U.S.
Favorite productivity habit
Heavy use of Slack and huddles, with a preference for avoiding recurring meetings.
Outside interest
Cooking — he used to work as a cook and still loves it, though he dislikes cleanup.
Bottom Line
This episode is a strong example of how a technical founder can learn sales by staying close to the customer and iterating through early mistakes. Shahar’s biggest lessons are that:
- Founder-led sales is often unavoidable early
- Technical differentiation only matters if customers can understand the value
- Pricing and positioning evolve as confidence builds
- Replacing incumbents like Datadog requires both product maturity and a new sales motion
GroundCover’s journey shows how a company can move from a narrow early use case to a broader displacement strategy once the product, market timing, and founder confidence all align.