Head of Operations

SkillBench, Inc.

$170K — $190K *
US-AnywhereRemote in United States
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6-8+ years in operations, with 3+ years at a venture-backed startup (seed to Series B)
  • Direct experience with US C-corp infrastructure: payroll, benefits, and compliance
  • Fluent in financial operations, partnering effectively on budget and headcount models
  • Experience managing a small team while actively contributing as an individual contributor
  • Strong coordination skills in a fast-paced, cross-functional environment
  • Exceptional written communication skills for clear operational direction
  • Willingness to work across time zones, preferably Pacific time for Asia overlap

Responsibilities

  • Drive cross-functional deployment coordination between sales, product, and customer success
  • Collaborate with the fractional CFO on budget management and strategic finance projects
  • Set hiring strategy and planning with the executive team, ensuring candidate experience aligns with company stage
  • Provide strategic direction for Asia operations, managing HR and administrative functions through the Korea Ops Lead
  • Establish operational norms for a distributed team to unify operations across locations
  • Own US operational infrastructure and compliance for a growing C-corp
  • Manage vendor relationships and corporate governance policies to support company growth

Benefits

  • Fully remote with flexible hours
  • Company and team offsites 2-3 times a year
  • Competitive medical, dental, and vision insurance
  • Company-provided laptop and a $1500 home office stipend
  • Flexible PTO policy
Full Job Description
About the Role - Why This Role, Why Now

SkillBench is defining a new category at the intersection of AI, developer workflows, and workforce transformation, and the enterprise market is already pulling. The first enterprise customers are live, and a growing pipeline of F2000 companies are buying. The team is distributed across the US, Korea, and Taiwan, scaling from 13 to 39+ people while running simultaneous enterprise deployments, a B2B and B2C product buildout, and a fundraise with some of the most recognized names in tech.

This pace creates an operational challenge worth taking on. We need an experienced startup operator to own US operations (legal, insurance, vendor contracts, corporate governance, talent, finance, deployment coordination) and to build the operating system that lets the rest of the company move fast without losing track of what matters. You'll report directly to the CEO and manage two direct reports: a Korea Ops Lead who manages HR, payroll, and administration for the Asia-based team, and a Talent Lead who runs recruiting. This is a hybrid IC/manager role. You'll set operational strategy and provide direction for your team, and you'll also be hands-on building systems, running processes, and closing gaps yourself. You are overall accountable for operations across both the US and Asia.

This role scales with the company. You're building the operational foundation for what comes next.

Location

US-based, remote. Pacific time zone preferred. Overlap with Asia business hours matters for this role given the Asia-based team.

What You'd Do
  • Drive cross-functional and deployment coordination. This is the highest-impact part of the role. You sit between sales/GTM execution, product/engineering delivery, customer deployment, and hiring. When a deal signs, you own the operational path to "customer live": tracking readiness, surfacing dependencies, and coordinating across Sales, Product, and CS leads so handoffs between functions stay clean.
  • Partner with the fractional CFO on finance. The company is signing its first ARR deals and standing up a more mature finance function. You'll work with the fractional CFO on budget management, cash flow planning, consolidated monthly close, fundraise-related financial modeling, and strategic finance projects like pricing model operationalization and headcount planning scenarios. You own prioritization for strategic finance.
  • Own hiring strategy and prioritization. The Talent Lead runs recruiting day-to-day. You set the hiring plan with the exec team, sequence roles against budget and business needs, and make sure candidate experience matches the company's stage and pace.
  • Provide strategic direction for Asia operations. The Korea Ops Lead manages day-to-day HR, payroll, and administration for the Asia-based team, owns the Korea subsidiary close, and handles hiring operations for any Asia-based roles. She also plays a key role in designing a cohesive company culture and employee experience that works across the US and Asia, differing where appropriate. You provide the strategic direction, build company-wide policies and operational foundations, ensure alignment with budgets and cross-regional operations, and hold overall accountability for operations across both regions.
  • Establish operational norms for a distributed team. Set up cadences and systems that work across time zones and employment models (FTE, contractor, academic affiliate). A globally distributed team needs to operate like one company, not multiple disconnected offices.
  • Own US operational infrastructure. Manage and fill gaps in compliance, payroll, benefits, state registrations, employment law, insurance, tax filing coordination, and audit readiness for a US C-corp. Some of this is already in place, the rest needs to be built or tightened up.
  • Own vendor management, corporate governance, and internal policies. Build and maintain the systems that keep the company running as it grows.

Requirements

What You Bring
  • 6-8+ years of experience in operations, with at least 3 years at a venture-backed startup (seed through Series B). You've built operational systems in environments where they didn't exist yet, while the company was shipping and selling around you.
  • Direct experience running US C-corp infrastructure: payroll, benefits administration, state compliance, employment law. You've actually done this, at a company where it was your problem to solve.
  • Financial operations fluency. You don't need to be a CFO, but you need to be comfortable partnering with one: managing budgets, building headcount models, and supporting fundraise-related financial work.
  • Experience managing a small team (2-4 people) while still doing significant IC work yourself. You want to build, not just oversee.
  • Strong cross-functional coordination skills in a fast-moving environment. You've managed dependencies across sales, product, and engineering timelines and know how to keep people aligned without adding process for its own sake.
  • Excellent written communication. In a distributed company, clear writing is how operations actually works.
  • Comfort operating across time zones. Pacific time is preferred for Asia overlap, and you'll work closely with the Asia-based team.


Nice to Have
  • Experience with international subsidiary operations, particularly in Asia (Korea, Taiwan, or similar markets).
  • Background in developer tools, AI/ML products, or enterprise SaaS. You'll ramp faster on the context if you've lived in this world.
  • Experience supporting a company through a fundraise from the operations side (data rooms, financial modeling, due diligence coordination).


What You Don't Need
  • You don't need COO or VP Ops experience at a 200+ person company. This is a seed-stage startup. What matters is that you can build operational systems, not that you've run mature ones.
  • You don't need deep technical expertise. You should be comfortable working alongside engineers and understanding product timelines, but this role doesn't involve any technical oversight.

Benefits

Compensation
  • The expected base salary for this role is $170,000-$190,000, with significant early stage equity. This is a co-builder role. The comp reflects that.

Benefits & Perks
  • Fully remote with flexible hours
  • Company + team offsites 2-3x per year
  • Competitive medical, dental, and vision insurance
  • Company provided laptop; $1500 home office stipend
  • Flexible PTO policy

Similar Jobs

More Jobs at SkillBench, Inc.

  • Head of Operations
    $170K — $190K *
    Remote
    Enterprise Technology
    Remote in United States

More Enterprise Technology Jobs

Find similar Head of Operations jobs: