Director or Vice President of Operations

Cortico.ai•Boston, MA

1d•Remote

About The Position

Cortico is a non-profit organization dedicated to fostering constructive conversations and surfacing underheard voices through intentionally designed and deployed technology. Their platform brings people together in recorded small-group conversations, utilizing a powerful combination of AI and human listening to help organizations understand these dialogues and integrate community voices into public discourse and decision-making. This platform has been successfully used in various contexts, including police chief selection, mayoral elections, local news reporting, global climate conversations, and amplifying marginalized experiences through artist collaborations. Cortico's unique human/machine system is a collaborative effort with MIT's Center for Constructive Communication (MIT CCC). Cortico is seeking a Director or Vice President of Operations, with the specific title to be determined by the candidate's experience and the scope they bring to the role. This individual will work closely with the CEO and the leadership team, serving as a connective tissue across the organization. Key functions include identifying areas that require attention, translating priorities between different teams, and ensuring a smooth flow of information throughout the organization. The role encompasses responsibility for finance, nonprofit compliance and governance, vendor relationships, and cross-functional coordination, while also keeping leadership informed of operational realities. The successful candidate will act as a chief of staff to the CEO, discerning when to escalate issues and when to handle them independently, and developing systems and instincts to manage both effectively. This position involves a blend of administrative and strategic tasks, ranging from conducting audits to facilitating leadership planning sessions. It is an ideal opportunity for a high-potential operator who is meticulous with details, broadly curious, and energized by building systems that enhance collaborative work.

Requirements

5+ years of professional experience spanning financial and operations management, ideally in nonprofit or mission-driven organizations.
Demonstrated comfort with building and managing budgets, overseeing financial reporting, and maintaining compliance. You don’t need to be a CFO, but you need the instincts of one.
Proven ability to manage multiple workstreams, keep systems running, and hold the details without dropping the ball.
Strong organizational skills with experience operating in Google Drive, Slack, QuickBooks, and CRMs.
Strong written and verbal communication skills, with the judgment to know when to escalate, when to act, and how to navigate sensitive organizational dynamics.

Nice To Haves

A good head for numbers and an eye for detail.
Comfort with budgets, financial statements, and cash flow, and ability to notice when something feels off before anyone else does.
Knowledge of the nonprofit world from the inside, including experience with audits, grant reporting, 990s, or board governance, and understanding what it takes to run a mission-driven organization well.
Ability to thrive when things are a little messy, wearing multiple hats, navigating ambiguity, and figuring it out alongside good people.
Ability to build trust quickly, read the room well, and help others feel connected to what's happening across the organization.
Comfortable in a spreadsheet as well as in a strategy conversation, able to zoom in on the details and zoom out to the big picture, and genuinely enjoy both.
Enjoy making things better; clunky systems don't frustrate you so much as invite you in, and you're excited to try new tools, including AI, to help the team work smarter.
Care about the work; Cortico's commitment to equity, inclusion, and community-centered practice resonates with you, and you want your day-to-day to reflect what you believe in.

Responsibilities

Own Cortico's financial operations end-to-end: budgets, cash runway, audit readiness, and day-to-day transactions.
Hold the keys — accounts, vendor payments, financial reporting — and be accountable for the organization's financial health.
Manage relationships with external financial partners, including our CPA and compliance advisors.
Ensure the organization stays audit-ready and meets all regulatory and reporting obligations (990s, grant reporting, board governance).
Build and maintain the systems and processes that let the team do their best work.
Own and manage relationships with legal, compliance, and other key external advisors.
Manage internal timelines and coordinate across leadership to ensure timely preparation of quarterly board materials.
Coordinate the annual CEO performance review and board self-assessment.
Occasionally coordinate travel and logistics for in-person team gatherings, workshops, and conferences.
Serve as the connective layer between the CEO and the team: surface priorities, translate team dynamics, and know what needs escalation versus what you can run with.
Push back when needed — we want your instincts, not just your execution.
Keep programs, product/engineering, media, and operations coordinated and moving — spot emerging issues early by staying curious and plugged in across the org.
Manage payroll and HR administration through a PEO, serving as the primary relationship manager.
Support the planning and execution of team engagement initiatives, with a genuine interest in fostering a strong team culture.