Skyler Holobach — Fractional Head of Product & Product Operations Leader
Athens, GA · Available for fractional and consulting engagements via Threadsmith Group.
I build the systems and features that get companies acquired. 13+ years in B2B SaaS product and operations leadership, including 4+ years as the CEO's execution arm across product, operations, and cross-functional initiatives.
Senior product and operations leader with a track record of building from scratch in ambiguous, resource-constrained environments: enterprise products, operational processes, compliance infrastructure, and the organizational systems that make scaling possible.
The throughline across roles is ownership of problems that cross departments, don't have an obvious home, and need someone to figure them out and drive them to completion. Trusted by engineering for technical fluency and clear prioritization, and by executive leadership as the person who translates strategy into executable plans.
She runs engineering and product operations for teams that are almost great and want to be great — called in when velocity has stalled, when senior talent is burning out, or when leadership can feel the ceiling but can't name it. Her last team shipped so fast that marketing asked them to slow down. She built the routing engine that got the company acquired — championed it, spec'd it, wrote every JIRA ticket, and was the reason it shipped on time.
SocketLabs — VP, Product Design & Customer Experience (2021–2026)
Promoted from Director in 2022. Served as Head of Product in a high-growth B2B SaaS environment, owning product direction across core platform infrastructure, reporting and analytics systems, growth surfaces, and enterprise customer tools.
- Built the highest-performing engineering organization in the company's history by establishing clear decision ownership, measurable roadmap outcomes, and a durable product operating cadence.
- Took 2 net-new enterprise products from concept to launch: an enterprise email infrastructure platform and a reporting & analytics product. Authored 2,000+ implementation tickets.
- Built the enterprise product stack that converted accounts from month-to-month to multi-year contracts and closed the 3 largest deals in company history.
- Contributed to 25% year-over-year revenue growth through product-led improvements tied to adoption and platform reliability.
- Reduced operational and support burden by 64% by identifying the single largest driver of manual ticket volume and eliminating it at the product level.
- Defined, specified, and drove adoption of an API-first platform architecture internally — the foundation that made enterprise deal flow possible.
- Self-taught Figma to close a critical design gap, producing production-ready UX specs and reducing design iteration cycles by more than 80%.
- Integrated AI-powered analytics through a Thoughtspot partnership, enabling natural-language querying of platform data for enterprise customers.
- Designed and ran the company's single most effective cross-functional forum, convening engineering, R&D, DevOps, support, and compliance leadership weekly.
Salesforce — Senior Manager, Privacy & Abuse Management (2018–2021)
Promoted from Manager in 2020. Selected as a top 10% leader; completed advanced leadership development focused on managing managers.
- Led global compliance and abuse management teams processing over 150,000 cases annually in close partnership with legal and product teams.
- Saved $680,000 annually by leading an email infrastructure migration, delivered 9 months ahead of schedule.
- Maintained zero attrition over seven years by building a high-clarity, supportive leadership environment.
- Served as the primary escalation point for ISP abuse desks, Spamhaus, and external complaints, directly protecting global IP and domain reputation.
- Led the successful merger of Pardot and Marketing Cloud abuse teams; migrated internal tooling from Desk.com to Service Cloud.
- Drafted and enforced company-wide permission-based marketing policies aligned with legal requirements and operational realities.
Pardot — Email Reputation Manager (2013–2018)
- Volunteered into and defined a new role by writing the job description, self-teaching the domain, and building foundational processes from scratch.
- Subject matter expert for email deliverability, compliance, and abuse prevention across the Pardot platform.
- Established and maintained relationships with ISPs and blocklist operators to resolve reputation issues at scale.
- Authored 86 posts for the Pardot blog, contributing to customer education and brand authority.
Volunteer Leadership
Board Member & Anti-Harassment Chair, Women of Email — a global professional nonprofit serving 8,000+ members across 50 countries. Entrusted with community governance, safety, and high-sensitivity escalation.
Education
B.S. Psychology, University of Georgia.
Portfolio — Shipped Product & Engineering Work
Full portfolio at threadsmithgroup.com/portfolio.
Led the transformation of the SocketLabs engineering organization into the highest-performing team in company history. Established clear decision ownership, measurable roadmap outcomes, and a durable product operating cadence in a group that had previously been the org's black sheep.
Email industry-changing features that allow vendor-agnostic email routing and traffic overflow. Email Relay routes mail across SendGrid, Mailgun, Sparkpost Bird, SocketLabs' Hurricane MTA, and generic SMTP — without code changes or risky migrations. Rule Engine sits on top for attribute-based routing across providers.
App-and-hardware combo (Arduino + custom mobile app) that lets Skyler control her bed remotely from her phone.
Custom to-do system built for her own household — her favorite personal build.
Part 2 of Chorelette. Chore-roulette: assigns household tasks unpredictably to keep things interesting.
Smaller PDF exports from Figma. Built because Skyler is a Figma superfan who wanted the export sizes to stop being a problem.
Browser extension that eliminates manual data entry into a legacy labor tracker. Built because typing information manually does not, in fact, build character.
LinkedIn's scheduled-posting flow takes far too many clicks. Skyler fixed that.
Recipe organizer built to solve the Pinterest recipe-hoarding problem. All the pins, actually organized and actionable.
The interactive portfolio site itself, built from scratch as a top-down desk metaphor with a notebook chapter interior. Purposefully non-templated to reflect the operator behind it.
Video Series
Skyler is producing Enjoy Your Time Off! And other things I wish people would stop saying to me: a layoff survival guide for high-performing women — a video series on YouTube.
Skills & Tools
Cross-Functional Execution and Organizational Operations · B2B SaaS Product Leadership and Strategy · Process Design and Operational Infrastructure · Stakeholder Management and Executive Communication · Risk, Compliance, and Trust Domains · Metrics Definition and Product Analytics · 0-to-1 Product Development · Product Discovery and User Research · Product Roadmap Development and Prioritization · Go-to-Market Strategy and Execution · Enterprise Product Management · Product-Led Growth · OKRs and KPI Definition · Agile and Scrum Methodologies · API Product Management · Data-Driven Decision Making · Applied AI and AI-Assisted Product Development · Technical Tradeoff and Decision Making · Figma · Aha · JIRA · Cursor · Claude · ChatGPT · Monday.com · Lucid · Microsoft Office · SQL
