Executive Assistant
S. Sutton & Associates Inc.
Toronto, ON

Title: Executive Assistants

Function: Central Operations

Location: Remote, Freelance, United States or Canada

Reports to: Principal, Direct Reports

Cohort: Core Staff

Hours: Flexible / Part-Time / 20-80 hours per month

Relocation Support: No

Apply: Please see the Join Our Team section of theS. Sutton & Associates Inc. website(www.ssutton-and-associates.com) and use the APPLY HERE button to upload your resume and cover letter consolidated into one document. Candidates will be contacted and interviewed on a rolling basis.

We are S. Sutton & Associates Inc. a philanthropic management consulting firm, serving nonprofit organizations and philanthropists. As dedicated specialists, we bring an understanding of best practices and experience across North and South America, Europe, Asia and the Middle East. Our decades of experience in all aspects of strategic planning, governance and fundraising enables us to provide ideal strategies and approaches to realize organizational success and the vision of leading philanthropists.

Built on an agency model, we draw upon a network of high performing technical experts to assemble customized Innovation Teams to meet each client’s unique needs. Our Associates are freelance consultants who, at their discretion, accept consulting engagements and who have the flexibility to work full - or part-time and from any location they choose.


You will be part of an international consulting firm led by recognized leaders in philanthropy. Through our unique Innovation Team Model, Associates of the firm:

  • Accept consulting engagements as desired
  • Benefit from an attractive compensation and incentive structure
  • Revitalize their professional experience and profile
  • Gain experience in State, Provincial and International markets
  • Build an exciting alternative - or complement to - full-time employment

We are proud of what we have built and are even more excited about our future. If you are the right person, we are excited to share our opportunities and success with you. Our projects attract a large network of smart, team-oriented professionals drawn to an entrepreneurial and creative environment. We work hard together, play hard together, and we support Associates to be successful individually and as a team.


We are looking for dynamic, driven Executive Assistants who can work with little direction to support the Principal and/or their direct report.

A successful EA manages and assumes responsibility for the Principal’s and/or their direct report’s agendas, effectively and proactively prioritizing on behalf of the Principal or direct report in appropriate situations. You make decisions and give guidance to others based on knowledge of the clients and Senior Leadership Team (SLT) members’ preferences. We need you to identify and manage the right priorities and processes to ensure that the Associates we support have what they need to seamlessly serve the needs of our clients. You solve problems before anyone knows that a problem exists.

This position involves booking (and unbooking) travel, scheduling (and rescheduling) meetings, keeping track of time and expenses, supporting the SLT process, and generally doing your best to keep up with the fast pace of our growing firm. While many members of the SLT are local, others are in the US, and the firm, when fully built will have Associates in 55 cities in 4 Provinces, 28 States and Washington D.C.

EAs are expected to grow throughout their careers, building and improving their skills to match the evolving needs of the firm and our clients. We won't define a career path for you – as the firm grows there will be several roles filled that will involve ever-increasing levels of experience with the firm and expertise. Joining us in these early days assures having an advantage as we build out the team. Your career will be at the intersection of your skills and desires and the needs of our business; it will only be limited by your investment.

EAs are an essential part of the cultural fabric of the firm. EAs actively participate in the virtual office life, are flexible and willing to help fellow team members, collaborate across functions, and serve as mentors to more junior members of the administrative team.


  • Provide high-level executive support for the Principal or direct report in a fast-paced and changing client service environment:
  • Organize and schedule client and internal meetings and events with an understanding of business priorities – proactively manages extremely complex calendars
  • Proactively manages and drives SLT team logistics
  • Effectively prioritize client needs (both within and across different teams)
  • Anticipate and coordinate point-to-point travel needs as necessary including booking all travel and hotels, directions, commuting time and ground transportation
  • Process timesheets and expenses on a timely basis
  • Prepare proposals, letters, slide decks, client invoices, etc.
  • Proactively support business development efforts
  • Assist with preparation of SLT materials and basic PowerPoint/Excel tasks – prepare slides, proposals, and other documents, including proofreading, editing, copying, and binding when required
  • Draft and archive correspondence
  • Provide backup support to other SLT members on a regular basis
  • Maintain high levels of confidentiality
  • Support administrative aspects of the Principals’ internal commitments: business unit activities, SLT meetings, recruiting, etc.
  • Act as thought partner and trusted advisor to SLT members and others in the firm.
  • Make sure they know what they need to know
  • Guide them toward making right decisions about use of time
  • Loop in all relevant parties when needed
  • Build effective working relationships with key stakeholders:
  • Clients and SLT members – understand preferences relating to travel, calendar, etc.
  • Clients and their Assistants – facilitate the scheduling process and relevant communications
  • EA and peers – work together to support other SLT members and Associates; provide back-up assistance as needed
  • Firm peers and internal resources – obtain and share information with wider team as needed; help SLT navigate internal resources
  • Perform other duties as assigned or required; responsibilities will vary


  • Bachelor's or college degree (strongly preferred)
  • Demonstrated leadership and/or customer service experience
  • Minimum of 5 years administrative support experience in a fast-paced environment (really fast paced!) supporting senior executives. Professional services industry strongly preferred


There are a few key things we look for – do you have what it takes to step into these shoes? Candidates who thrive at S. Sutton & Associates Inc. possess the following attributes:

  • High customer service orientation – highly responsive, strong interpersonal and communication skills, wants to deliver great results at all times.
  • Sweat the small stuff – strong attention to detail and accuracy, particularly when under pressure.
  • Dedicated to the work we do – committed to making our clients and Associates successful.
  • Proactive – looking ahead at what needs to be done on all dimensions; creates own to do list.
  • Organized – excellent at time and project management, has clear systems and composure to deal with multiple tasks at once and ensure everything gets done in a timely manner.
  • Relationship-oriented – extremely people focused with a certain 'joie de vivre' and the ability to develop effective working relationships with the clients, the senior leadership team (SLT) and the wider Associate network.
  • Good judgment – highly professional and diplomatic, knows when to ask for help or advice, perceptive and practical.
  • Trustworthy – discreet (you will be privy to confidential information).
  • Flexible – must be able to perform successfully in a fast-paced environment; doesn't get frustrated by priorities changing; open to feedback.
  • Team player – proactively seeks opportunities to help others, will go above and beyond in order to get the job done.
  • Committed to improving the status quo – we respect and hire people who are willing to ask questions, people who will say what's on their minds and are willing to make a suggestion, even if it is turned down.
  • Strong intellectual curiosity – a creative thinker, interested in the big picture.
  • Self-motivated – a "can-do" attitude with an entrepreneurial spirit and a desire to take on an increasing level of responsibility. As you grow in the role we expect that you will be increasingly proactive.
  • Demonstrate a high level of ownership of tasks and sound business judgment.
  • Be seen as a key contributor to the team process.
  • Demonstrated ability to fulfill responsibilities remotely and in a virtual environment
  • Demonstrated ability to work with variable teams in diverse environments on behalf of a wide range of clients
  • Exceptional written and verbal communication skills
  • Outstanding organizational and prioritization skills
  • Superior attention to detail, professionalism, and good judgement

Job Types: Part-time, Contract, Freelance