GoodPlan is hiring a full-time Executive Assistant to support the CEO, and the firm's operations and business development. This role is a front-row-seat to scaling a start-up.

Executive Assistant

GoodPlan is hiring a full-time Executive Assistant to support the CEO, and the firm's operations and business development. This role is a front-row-seat to scaling a start-up.

Employment Type: Full-Time

Reports To: CEO

Location: Remote; U.S. Based required; Chicago preferred, but not required.

Timezone: Central or Eastern time zone required

Salary Range: $65,000 - $75,000 with benefits

Application Deadline: Before Friday, October 30 at 4 PM CT / 5 PM ET

About GoodPlan

GoodPlan is a social impact consulting firm partnering with nonprofits, foundations, philanthropists, and social enterprises addressing complex social challenges. We apply rigorous strategic thinking and disciplined execution to help mission-driven organizations operate with clarity, focus, and long-term sustainability.

We work directly with CEOs and senior teams to clarify strategic priorities, define tradeoffs, align capital and talent, and strengthen operating models. We bring deep experience across the social impact sector paired with disciplined business judgment — grounding mission-driven ambition in sound strategy, institutional reality and financial capacity.

We focus on outcomes for our clients — strengthening education systems, expanding access to affordable housing, advancing immigrant opportunity, and creating durable workforce pathways. Our work aligns strategy with execution, ensuring social impact organizations operate with focus, financial discipline, and the institutional capacity required to deliver sustained, measurable impact.

An opportunity to build

GoodPlan is a growing firm, and this role sits at the center of it. You'll work side by side with the founder/CEO, see every part of the business, and help build the systems, processes, and rhythms that let a small team scale well.

This role supports the CEO in building and executing repeatable business processes and systems. The CEO will make "it" up, and this role will make "it" real and make "it" repeat.

Making "it" real means taking an idea and building the workflow, template, checklist, or automation. Making "it" repeat means running it reliably every week, every month, and every engagement, without being reminded. We want someone who is excited by both of these things – and cares equally about the process on its fifth and on its hundredth run.

Why GoodPlan?

Entrepreneurial Culture. You won't sit on the sidelines. You'll work side by side with GoodPlan's founder, see the whole business, and have real ownership over the processes that guide how the firm runs.
Professional Growth. You'll have the opportunity to stretch and grow as an operator and process manager, with real support and investment in your development.
Work That Matters. Our clients are moving the needle and having lasting impact on communities and causes you care about. The systems you build make that work possible.
Trust and Flexibility. We are a small team that operates remotely with autonomy and high standards. We work closely, communicate clearly, and treat each other with respect, empathy, and professionalism.

This position is for you if you are:

Excited to build. You want to be at the center of scaling a business, and you enjoy turning a rough idea into a system that works.
Committed for the long haul. You want to build something and stay to run it. A well-kept system is its own reward.
Entrepreneurial. You see what needs doing and do it, and you're comfortable starting without a playbook and building one as you go.
Flexible. A pipeline question, a calendar conflict, a vendor renewal, and a family logistics item can land in the same hour. You triage well and keep your footing.
Exceptionally reliable. Follow-ups are handled. Details are tracked. Nothing falls through the cracks.
Comfortable with numbers. You'll send invoices and run financial reports. We'll teach you how, but you should feel at ease with executing tasks related to finances.
Technically fluent. You learn new tools quickly, configure them properly, and look for ways to automate what repeats.
Discreet. You handle confidential business, financial, and family information with judgment and care.
Motivated by impact. You care about expanding opportunity and strengthening the institutions that serve society.

Your Responsibilities

The CEO partners with you on much of this work. We'll teach you how we do things, and it will be your job to run the plays, track the follow-ups, and move the ball forward. We anticipate your time will be distributed relatively equally across the four areas described below.

1. CEO Support: helping the CEO be at his best, professionally and personally

Manage the CEO's calendar, including scheduling, conflict resolution, and protected time for focus and family
Triage the inbox daily, drafting replies and making sure no client, prospect, or partner communication goes unanswered
Prepare briefing materials ahead of meetings, and capture and route commitments afterward
Book travel and build itineraries for client, conference, and personal trips
Coordinate family calendars, appointments, and school and activity logistics
Handle personal administrative tasks such as renewals, forms, insurance and benefits claims, and personal research and planning

2. CEO Project Management: helping the CEO execute the projects that build the firm

The CEO is always working on a range of projects to build the firm, and they change. Recent examples include launching new services, setting up the company 401(k) plan, running cash flow analysis, and negotiating contracts. You'll help project manage the CEO through an ever-changing list of internal projects..

Keep a running list of the CEO's active projects, with next steps and deadlines, and drive each one forward
Break projects into tasks, track them in Asana, and follow up until they're done
Do the legwork: research options, gather information, compare providers, and bring back a clear recommendation
Gather financial data for the CEO to run the analysis.
Keep contracts and negotiations organized through to signature
Surface what's stalled, what's due, and what needs a decision
Coordinate and follow up with other teammates on delegated items

3. Firm Operations: building and running the process machinery of the firm

Administer the firm's technology stack across Google Workspace, Asana, HubSpot, Harvest, and Gusto, including accounts, permissions, security hygiene, and offboarding
Send invoices on schedule, track time entry in Harvest, process expenses, and prepare regular financial reports for the CEO, working with bookkeeping
Track client and vendor contracts, including SOWs, renewal dates, and executed copies
Run payroll and HR administration in Gusto, including benefits and tax notices
Serve as the day-to-day liaison with the firm's attorney and other outside advisors
Support the administrative aspects of GoodPlan’s recruitment and hiring processes
Manage onboarding workflow for new team members, from accounts and equipment to first-90-day checklists,
Manage vendors, subscriptions, and renewals
Document how the firm operates through SOPs and checklists, and keep them current as the firm grows

4. Business Development Support: helping the CEO follow up and keep the pipeline moving

Maintain HubSpot as the system of record, with a clear next action and date on every prospect and opportunity
Manage HubSpot tasks and reminders, and run the follow-up with prospects so nothing goes stale
Prepare pipeline reports and materials for a recurring pipeline review with the CEO
Draft prospect meeting recaps and follow-up correspondence for review and sending
Research prospects ahead of introductory meetings, and coordinate proposal and SOW logistics
Create agendas and updates for business development meetings with team members and prospective clients

We want you to have:

5+ years of experience in executive support, business operations, or a comparable role
Experience in a startup, small business, or founder-led environment (a plus)
Comfort with financials. You'll send invoices and prepare reports for the CEO, who will teach you our approach
A track record of building or improving processes and then running them consistently over time
Fluency in Google Workspace and Asana, along with HubSpot or a comparable CRM, and comfort administering software
Skill in using AI tools to organize work and automate repeatable tasks
Experience with payroll or HR platforms such as Gusto (a plus)
Exceptional organization, attention to detail, and the ability to drive timelines
Strong written communication and the judgment to draft on behalf of a CEO
Demonstrated discretion with confidential business, financial, and family information
Comfort in an entrepreneurial, fast-paced, fully remote environment
Bachelor's degree preferred
Central or Eastern time zone required

You will get:

A front-row seat to building and scaling a firm, with direct access to the founder/CEO
Salary of $65,000 - $75,000, plus benefits including health, dental, vision, retirement contributions, and paid time off
A structured 90-day onboarding, with a weekly one-on-one with the CEO, so you know what success looks like at each stage:
Days 1–30, learn how GoodPlan works. Set up your tools, take over the CEO's calendar and inbox, and handle invoicing and HubSpot follow-up alongside the CEO.
Days 31–60, own the recurring work. Run the weekly rhythms (calendar, inbox, invoices, pipeline follow-up) and start project managing the CEO's active projects.
Days 61–90, build and improve. Document the processes you run, propose your first system improvement, and hold a 90-day review with the CEO.
Ongoing investment in your professional development
Flexible, remote work arrangements grounded in trust and clear expectations

How to apply:

Applicants may apply here before Friday, October 30 at 4 PM CT / 5 PM ET. Selected candidates will be invited to interview. Questions? Contact us at hello@goodplan.co.

GoodPlan is an equal opportunity employer and does not discriminate on the basis of any protected characteristic under applicable law. We believe diversity strengthens our work and encourages applicants to apply who bring varied life experiences, identities, and perspectives.

Executive Assistant