We are a small, growing insolvency and restructuring firm looking for a highly organized, resourceful, and discreet Executive Assistant to serve as the CEO's right hand. The role may also provide support for our four Licensed Insolvency Trustees (LITs).
This role has two distinct dimensions. First and foremost, you'll work in close partnership with the CEO — understanding their priorities, working style, and communication preferences well enough to anticipate needs, make judgment calls on their behalf, and represent their voice to internal and external stakeholders when they're not available. Second, you may help to support and coordinate scheduling and logistics for the broader trustee team, ensuring the leadership group's time is optimized, and their public-facing presence stays polished.
The ideal candidate has real experience being the trusted right hand to a senior executive — ideally in a small or founder-led company, where the EA role naturally expands beyond calendar and admin work into business operations, informal chief-of-staff type functions specific to the CEO and suggesting or driving improvements to internal processes and communications. You operate with high integrity, thrive on structure, anticipate needs before they're voiced, and take pride in being the person everyone can count on to keep things moving.
You'll directly enable the CEO and trustees to spend more of their time where it matters most: working files, meeting with referral sources and clients, and growing the firm
Key Responsibilities
CEO Partnership & Executive Support
- Serve as the CEO's primary point of coordination and trusted right hand — understanding their priorities well enough to make decisions and triage on their behalf
- Anticipate the CEO's needs, preferences, and upcoming demands proactively, reducing the need for explicit direction over time
- Represent the CEO's voice and priorities to internal staff and external stakeholders when the CEO is unavailable
- Exercise sound, independent judgment on behalf of the CEO in ambiguous or time-sensitive situations
- Handle sensitive internal and leadership-level information (not just client-facing matters) with complete discretion
Calendar and Time Management
- Proactively plan long-term and short-term schedules, ensuring top firm priorities are identified and accounted for in calendars
- Manage complex, shifting calendars for the CEO prioritizing file work, client meetings, and referral-source relationships
- Proactively resolve scheduling conflicts and protect focus time for file work
- Coordinate meeting logistics (in-person, virtual, travel) including agendas and follow-ups
- Provide secondary scheduling support for four trustees
Administrative and File Support
- Assist with preparation, formatting, and proofreading of correspondence, reports, and client-facing documents
- Maintain organized digital and physical filing systems in line with firm and regulatory standards
- Handle expense tracking, invoicing support, and basic office administration
Client and Referral Source Relations
- Serve as a first point of contact for key clients, referral sources (lawyers, accountants, financial institutions), and other stakeholders
- Coordinate all aspects of key industry, client, and referral source meetings, including locations, logistics, cost management, on-site coordination (where needed), and follow-up
- Coordinate and help prepare materials for client and business development meetings
- Support a professional, responsive client experience across phone, email, and in-person interactions
Marketing and Social Media
- Coordinate day-to-day execution of the firm's social media presence (LinkedIn and other relevant platforms)
- Work with marketing support to ensure drafts, schedules, and posting of content; monitor engagement and flag opportunities
- Support marketing initiatives such as newsletters, event coordination, website updates, and promotional materials
- Help maintain a consistent, professional brand voice across all external communications
Office and Team Support
- Act as a central point of coordination between the CEO, trustees, associates and administrative staff
- Assist with onboarding logistics, vendor coordination, and general office operations where required
- Take on ad hoc projects as the firm grows
Experience Required
- 5+ years supporting a CEO or senior executive in a close, trusted working relationship; additional experience supporting a broader leadership team is an asset
- Demonstrated experience acting as a true right-hand or gatekeeper to an executive — building enough trust and understanding of their priorities to be delegated judgment calls, not just tasks
- Experience supporting a CEO in a small or founder-led company strongly preferred, where the role often extends beyond traditional EA duties
- Comfortable operating without established systems — able to build processes, not just follow them
- Experience in a professional services environment (law, accounting, insolvency, financial services) considered a strong asset
- Excellent written and verbal communication skills
- Strong working knowledge of Microsoft Office (Outlook, Word, Excel, PowerPoint), calendar management, and AI tools that support streamlining and organizing
- Comfort with social media platforms and basic content scheduling tools (e.g., LinkedIn, Canva, Hootsuite/Buffer)
- Exceptional organizational skills with the ability to juggle competing priorities across multiple stakeholders
- High degree of discretion and professionalism when handling confidential client, financial, and internal leadership information
- Self-starter who is comfortable in a small-team, entrepreneurial environment where responsibilities evolve
What we offer:
- The opportunity to grow with a small, entrepreneurial firm and take on increasing responsibility
- Direct exposure to leadership and the insolvency/restructuring profession
- Competitive salary, commensurate with experience
- Health and dental benefits, Health Spending Account, 3 weeks’ vacation
Hours:
Monday – Friday, 9:00-5:00
Salary Range:
$70,000-80,000 commensurate with experience.
If you are interested in applying for this position, please send your resume and cover letter to [email protected]
We thank everyone for taking the time to apply; only candidates selected for an interview will be contacted.
Job Types: Full-time, Permanent
Pay: $70,000.00-$80,000.00 per year
Benefits:
- Dental care
- Extended health care
Experience:
- Executive Administration: 5 years (required)
Work Location: In person
