Telecommut
This role is for someone who does.
This position sits in People and Talent Operations, but it is fundamentally a systems design and operations role, with hiring as the domain. You are not expected to be a subject-matter expert in hiring. You are expected to be an expert at building systems that deliver clear results — systems that are scalable, repeatable, and resilient under real-world pressure.
The problem to solve is simple to describe and hard to execute: design and operate a system that consistently brings the right people into the business, on time, at the right quality bar, and into roles where they succeed and stay. That system must work not just for clean, well-defined requests, but for ambiguous, high-stakes, non-standard ones too. This role requires ongoing ownership, good judgment, and the discipline to fix issues in ways that strengthen the system rather than adding complexity.
Stakeholder management is non-negotiable. You will work with senior leaders who have strong opinions, competing priorities, and imperfect inputs. You will not have formal authority. You will succeed by building trust, finding common ground, and clearly surfacing trade-offs — holding the quality bar while helping people feel heard and supported.
This is an AI-first environment. You will be hands-on with AI every day, using it to generate drafts, test ideas, analyze outcomes, explore edge cases, and surface patterns. You won’t hand ideas to engineers and wait. You’ll build, test, break, document, and iterate yourself, then partner with others when it’s time to scale or harden something.
We also want to be transparent, because we don’t want to waste your time. This is not a role for everyone.
If any of the following sound like you, this likely isn’t the right fit:
- You prefer diagnosing problems over owning solutions end to end
- You need authority, org charts, or formal DRIs to get work done
- You only work through engineers instead of getting hands-on yourself
- You see feedback or pushback as a personal attack rather than useful signal
- You focus on optimizing individual pieces and miss the system-wide effects
- You like the idea of fixing broken systems more than the reality of doing it
One last thing, in the spirit of honesty: our application process requires real effort. Most candidates invest meaningful time because the role itself requires it.
If reading all of this made you more energized — not less — we’d genuinely like to hear from you.
What You Will Be Doing
- Designing and improving end-to-end systems that turn ambiguous needs into repeatable, high-quality outcomes
- Working directly with senior stakeholders to clarify real constraints, surface trade-offs, and align on what “good” looks like
- Using AI daily to generate, test, analyze, and refine system components, then applying human judgment and quality control
- Owning your work from first idea through results, measurement, and iteration — no handoffs, no partial ownership
- Identifying patterns, diagnosing root causes, and improving the system based on outcomes and real-world feedback
A Head of Business Operations in this role will not be doing any of the following:
- Diagnosing problems and handing execution to someone else
- Optimizing one part of a system while ignoring downstream effects
- Waiting for authority, formal structure, or escalation to make progress
- Reviewing resumes or running first-round screening interviews
- Avoiding messy problems, difficult stakeholders, or accountability
Design, own, and continuously improve the systems that deliver high-quality hires on time and into roles where they succeed and stay.
Basic Requirements
- 5+ years of experience in business operations, people or talent operations, program management, or a similarly system-heavy role
- Direct experience hiring for your own team or function, with accountability for hiring outcomes (e.g., time-to-fill, quality, retention)
- Hands-on experience designing and implementing operational systems end-to-end, not just maintaining them
- Experience creating org and operating artifacts such as role specs, org charts, ladders, RACIs, workflows, or decision frameworks
- Strong written operator: has produced SOPs, process docs, or post-mortems used by others
- Working knowledge of U.S. hiring practices and regulations, including compliance considerations
- Comfort working directly with senior leaders without formal authority
- Practical, daily use of AI in operational work, with attention to quality and trade-offs
- Availability for at least 6 hours overlapping U.S. business hours on weekdays
- Experience taking a system through multiple iterations based on performance and retention data
- Familiarity with low-code tools, automation platforms, or agentic workflows
- Experience building dashboards or visualizations for executive audiences
- Background in high-growth, high-accountability, or private-equity-backed environments
Crossover has been a pioneer of the remote work model since our inception in 2014 - helping thousands of people advance their careers. We specialize in full-time, long-term remote jobs - not short-term "gigs" or part-time freelancing side ventures. Our platform provides businesses with the fairest hiring on earth by basing 90% of the decisions on objective assessments of a candidate's skills and abilities to perform Real Work. Since we are 100% remote, people can work from anywhere and earn standardized and competitive compensation, regardless of where they choose to live.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with Crossover
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5712-CA-Mississa-HeadofBusiness
