Hi! My name is Skyler Holobach. Welcome to Threadsmith Group!

I spent seven years at Salesforce working on compliance and trust infrastructure at scale, then went VP-level at a B2B SaaS company where I ran operations as the CEO's right hand. I scaled product orgs, turned around teams that were underperforming, and built the kind of operational machinery that lets a company run without one person holding every thread. On paper I was the leader people wanted: strategic, relentless, always available, always delivering.

I was also burning out, and I had a front-row seat to exactly why.

The systems I was fixing for the business were the same ones grinding people down. I saw roadmaps that changed with the founder's mood, decisions that routed through one exhausted person (me), and process that existed because…..well, um, someone built it 10 years ago and no one was brave enough to challenge it, but they sure could suffer through it. I watched it break the companies, I watched it break the people inside them, and eventually I was one of the people it broke.

I felt the kind of burnout that left me sobbing at 2:30 in the afternoon for no reason, the kind a vacation does not touch, because THAT IS NOT HOW BURNOUT WORKS. My full burnout story is here if you want it (part 1,part 2,part 3). The short version is that I completely unraveled, and I had to rebuild how I work, lead, and live to find my way back.

That rebuild is why Threadsmith Group exists, and it is why I do two kinds of work that are actually the same work. What I Do

For founder-led B2B SaaS companies, I fix the operational infrastructure underneath the business. I embed for 3-6 months, find what is actually broken versus what everyone thinks is broken, and build the decision frameworks, execution rhythms, and cross-functional alignment that let the founder stop being the bottleneck. Then I leave, because the entire point is that you do not need me forever.

For professionals and leaders who are burning out or already flattened, I do burnout recovery coaching. We get underneath what is draining you, build boundaries (SO important!!), and rebuild the stamina and clarity that the grind took from you.

High-performance cultures break systems and break people, usually at the same time and for the same reasons, and most of the standard advice treats the symptom while ignoring the rot. I have led engineering orgs, launched enterprise-level products as a 0-1 builder, and spoken at places like Unspam, M3AAWG, and Dreamforce. I also sit on the board of Women of Email. I know what SaaS cultures demand, and I know the wreckage they leave when nobody changes how the work actually happens.

While we worked on different teams at Salesforce, Skyler was a true cross-functional partner whose work deeply impacted my organization’s ability to successfully serve customers. She saved me hours per month by writing code to automate a process I’d previously been running through time-intensive manual work, a project she took on with enthusiasm and delivered with excellence. That level of clarity and vision is a hallmark of Skyler’s work, and it’s paired with compassion and a desire to improve processes across the business.
— Josie Harvey, VP of Customer Success at ServiceTrade

Why It Matters

Burnout is not a personal failing, and a thrashing company is not just a founder who needs to try harder. Both are signals that the way the work is structured has stopped being sustainable. I have lived both sides of that. I broke, I rebuilt, and I built a practice that helps founders fix the machine and helps people recover from what the machine cost them.

If you are here, you probably already feel the thing that is not working. My job is to help you fix it, whether the patient is your company or you personally.

Fun non-work info

I live in Athens, Georgia with my husband and never enough pets. I’m a collector of hobbies, with interests ranging from weaving and crochet to laser cutting and swordfighting. I contain multitudes. :)

Skyler personally manufactured over 5,000 units of protective face shields for local medical practitioners and first responders during the COVID-19 pandemic, as part of a volunteer effort that delivered over 60,000 units total. The fact that she as a single individual accounted for nearly 10% of our total deliveries is a testament to her unending commitment and consummate professionalism. Her ability to fully commit to a mission and lead others to success is inherent in her character.
— William Strika, CISSP, Lead Security Engineer, AT&T

It’s me!

Photo credit @johnmblood

Chat conversation with purple and black speech bubbles; someone is saying they are working on acceptance and finds it brutal, with heart emojis included.

Proof that I’ve been there too. :)

When Women of Email invited Skyler to join our Board of Directors, we didn’t anticipate what a profound impact she could make in such a short period of time. She doesn’t settle for the status quo, recognizes opportunities to lead positive change, and rolls up her sleeves to get it done. Her instincts are solid, her judgment is excellent, and her problem-solving capacity is rare.
— Jen Capstraw, Co-Founder, Women of Email

Contact us

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