Winston Bowden is a marketing executive with more than two decades of experience driving growth
at technology companies from early-stage startups to global brands.
He began his career as a marketing manager at the Center for Entrepreneurial Development
(CED) where he helped emerging technology and life sciences companies connect with capital
and resources. Following agency and startup leadership roles, Winston joined Mozilla, advancing to
head of integrated marketing for North America and remaining in the role for nearly a decade. In this role, he directed large cross-functional teams to expand Firefox’s global use base.
In 2020, Winston returned to his startup roots, joining Testim.io, where he accelerated growth and
helped position the company for its successful acquisition by Tricentis. He subsequently advised
and led marketing initiatives at multiple startups.
Winston currently serves as VP of marketing at Sawmills.ai, a seed-stage startup developing AI-
powered telemetry management solutions for the observability market. He holds a B.S. degree from East Carolina University.
1.) What is in your pockets?
I have a Journey GPS wallet and my phone. It contains GPS in case I lose it.
2.) What exciting thing has happened recently to you or your organization?
We came out of stealth mode earlier this year, landed, and raised a $10 million seed round.
Our company is called Sawmills.ai. We are the first smart telemetry management platform. For
companies to ensure that their applications are working and know their customers are getting the
optimal experience, they need to observe how users interact with their products.
Observability is the ability to really understand what’s happening inside the application to monitor it. Applications collect vast amounts of data, which they then send to the observability providers. This data is called telemetry data and it’s comprised of logs, metrics, and traces that help customers troubleshoot
and debug.
The challenge is that what ends up happening is that the majority of the data that companies send to these massive observability companies is unusable—and they have to pay for it. Many of
these companies are pricing based on the amount of data they ingest. Our founders did a survey and found that 87% of the data on average that is sent to these providers is junk. These bills can be millions of dollars.
We are not an observability provider. We sit on the customer’s side before the data is sent to the
observability vendor. We’re the smart telemetry management platform. We analyze the data with
our AI and filter it. We transform it to ensure that only the data that is necessary is sent to the
observability provider.
The key is we’re not just slashing data, we’re transforming it and making it
easier to ingest. The customers pay less for the data that the engineers actually need to debug
something. We’re one of the first players in this space. We have a strong pipeline in place and are getting great customer feedback from several big brands. We are really starting to launch our go-to market.
3.) What is your favorite coffee spot?
Heirloom in Downtown Raleigh. It has great coffee and chocolate chip banana bread and it is
walkable from where I live. It’s a local business, and the husband-and-wife owners are good
people. It’s a great, beautiful spot.
4.) What keeps you up at night?
On the personal side, the toxicity and division in our country. I am hopeful we will find ways to come
back together.
On the business side, the go-to-market landscape is changing so quickly. Channels that historically
were the bread and butter of our inbound go-to-market strategy are being turned upside down by AI.
Large language models (LLMs) are changing how people make purchase decisions.
Finding ways to get the LLM to spit your brand out, especially as an early-stage startup, is something that’s on everyone’s minds. Finding new ways to break through the noise and new channels is keeping
anyone who’s responsible for revenue growth up at night because the old model is out the door. If you are not trying new things, including some that had previously been sunsetted like old-school conferences, you are in trouble.
5.) What’s your favorite restaurant or happy hour?
I’ll often go to Williams and Company for happy hour and then Crawford and Son for dinner.
6.) What is next for you or your organization?
We’re focusing on building category and awareness around Sawmills as the leader in the telemetry
management space, which really doesn’t exist. It’s a space we are building.
[This involves] getting the message out to DevOps and platform leaders so they understand there is a better way forward, one that’s going to dramatically reduce observability costs. It will also improve the quality of their data, which will improve the quality of how they are monitoring, troubleshooting their applications, and providing customers with a good user experience. That means telling our story, growing brand visibility, and helping the market understand there is such a thing as AI-powered, smart telemetry management.
