Quick overview
Job description
About the job:
Hi, I’m Shane and I’m the VP of Finance & Ops at Ashby.
Ashby is in a high growth phase (growing more than 120% y/y with more than 5,000 customers), selling into SMB, mid-market and enterprise segments, and our legal function is at an inflection point. Today, that’s a strong team of 3 who are experienced in commercial work and legal ops. We’re hiring a Head of Legal to lead Ashby’s entire legal function and who is focused on scaling the legal team’s impact as fast as the rest of the business is growing. Your job is to broaden the legal function to cover everything a company like ours needs, personally owning our corporate work while deciding what we build in-house, where we lean on outside counsel, and when we add to the team. You’ll be the senior legal voice at Ashby and a close advisor to our leadership team. This is an ownership role, and you’ll operate with a significant amount of autonomy.
Every company says it wants legal to be a true business partner. Few build a legal function that actually works that way. Slow legal review doesn’t guarantee a safer company, but it does guarantee a slower one. The best legal teams understand the business well enough to know which risks matter, give clear guidance in plain language, and build the guardrails that empower business leaders to make good decisions. And when something really matters, they know exactly where to hold the line. That’s the function we want you to build. Please read Ashby’s Operating Principles and Leadership Principles to understand the operating environment and expectations we have of leaders.
Your initial responsibilities will include:
Leading Ashby’s entire legal function, including our existing commercial legal and legal ops teams, and expanding its coverage as the company grows.
Advising me and our leadership team, and personally owning corporate governance, strategic transactions, employment, and equity matters. You’ll provide clear and commercial advice across the business that is accurately risk adjusted and action oriented.
Designing the operating model for legal: setting the priorities, deciding what we handle in-house and what we send to outside counsel, and managing outside counsel quality and spend.
Building a practical and scalable approach to privacy, product, AI, and compliance matters as the regulatory landscape around data and AI continues to evolve.
Partnering closely with cross-functional stakeholders: Security on data protection and customer trust, Finance on corporate and strategic matters, People on employment issues, Product on how we build compliant products, and Sales on how we can close deals with high velocity.
Creating the frameworks, playbooks, tools, and systems that help teams at Ashby make good decisions and help a small legal team do outsized work.
You should apply if:
You have at least 12 years of legal experience, from a law firm to in-house at a high-growth tech company. You’ve led an in-house legal team, hiring, coaching, and managing lawyers directly, and you know what a legal team should look like at a company that’s moving fast.
Corporate law is your primary practice. You’ve handled governance, equity, financings, and M&A yourself, not just overseen outside counsel, and you’re ready to own that work as Ashby scales. You also bring real depth in at least one other area, such as privacy and regulatory, or compliance.
You see legal as a lever, not a blocker. You understand how the business makes money, its priorities and risk appetite, and look for the path to yes. When the answer has to be no, you explain why and bring forward a better option.
You build trust across the business. You’ve partnered closely with leaders in Finance, People, Product, Security, and Sales, and you know how to adapt to what each team needs. Business leaders seek you out early because you make their work easier, not harder.
You’re a generalist who’s energized by breadth. You go deep enough to make the call yourself and know when it’s time to bring in a specialist.
You make the people around you better. You’re excited to coach a small but mighty team and give them real ownership of their work.
You care about how the work gets done, not just the work itself. A well-designed workflow gives you as much satisfaction as a well-drafted contract.
Why you shouldn’t apply:
You expect a fully built legal department to step into. You’ll inherit a strong team and a solid foundation, but much of what a complete legal function covers is still yours to build. If you’d rather step into a finished system than build one, this won’t be the right fit.
You want legal to set the agenda. The best legal partners help the business bring its decisions to life, safely and well. If you’d rather drive those decisions than deliver on them, you’ll find this role frustrating.
You want legal to approve everything. If your instinct is to route every decision through legal rather than equip teams to move intelligently (and quickly) within the right guardrails, you’ll slow us down in ways we’re trying to prevent.
You’re skeptical that technology can change how legal works. We’re not. We want someone eager to try new tools and build systems that scale.
You want to manage outside counsel, not practice law. This is a hands-on role, and you and your team will be focused on executing and doing much of the work yourselves.
Your first instinct is to protect against every possible downside. Some risks are worth taking, and we need someone who can tell the difference and help us move quickly.
You default to replicating what you’ve done before rather than evaluating from first principles. At Ashby, one of our Operating Principles is to think from first principles and your recommendations and strategies will need to be tailored to what works best for Ashby.
You prefer an in-office environment. This is a remote role and is best-suited for self-starters who excel in an independent setting.
You’re uncomfortable with change. We are a rapidly growing team and company, and the ability to stay flexible and thrive amid change is key to success here.
Interview Process
Our interview process is thorough - we assess if you are the right fit for Ashby and we will provide ample information for you to determine if Ashby is the right place for you. The process for this role is as follows:
Recruiter Screen with Caroline- 30min
Hiring Manager Interview with Shane - 45min
Practical Assessment
Final Round - 2.5 hours
Benefits:
10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.
Unlimited PTO, and we will encourage you to take it.
A minimum of 12 weeks of fully paid parental leave, covered by Ashby. For folks outside the US, it may be longer to be in line with regional requirements.
Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!
$100/month education budget with more expensive items (like conferences) covered with manager approval.
If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. In other countries, we provide high-quality supplemental health insurance for you and your dependents, also fully covered by us.
401k match
Ashby’s success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We’re being deliberate about building that environment from the ground up. I hope that excites you enough to apply.
Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.