About Feathery

Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader in financial agentic automation. Industry leaders like Tokio Marine, Sequoia Financial, and Cerity Partners run their client-facing workflows on Feathery, from onboarding and risk assessment to reconciling systems and generating proposals and reports. At the center of it all is Robin, our AI operations assistant. Robin scans client documents, configures and deploys workflows, assists users in their day-to-day work, takes notes during meetings, and supports a growing range of operational tasks across the client lifecycle.

We're building a future where financial operations shift from paperwork, manual data entry, and disconnected systems to intelligent, automated workflows that let firms spend their time on clients instead of process. We're proud to be backed by world-class investors who share that vision, including Portage Ventures, Allstate Ventures, and Index Ventures, among others.

We're driven by a shared commitment to excellence and velocity. Our values — Own the Problem, Grit Beats Gloss, Say It Straight — shape how we work and grow as a team.

Why We’re Hiring

As Feathery's client base grows, we're looking for an Account Manager to own and grow a book of mid-market and enterprise clients. This role will focus on strengthening client relationships, driving renewals, reducing churn, and expanding existing accounts, while also supporting new business growth across the SMB and mid-market segments.

About the Role

As an SMB / Mid-Market Account Manager, you'll own and grow a book of mid-market and enterprise clients. You'll be the primary point of contact for these accounts, building strong relationships, driving renewals, reducing churn, and identifying current ways Feathery can support each client's business.



Most of your time will focus on managing your existing book of business, leading renewal conversations, reducing churn, and expanding accounts through additional volume, new use cases, and add-on products.

You'll also own new business for SMB and mid-market companies, running demos, closing deals, and onboarding new clients onto the platform yourself.

You'll work closely with Feathery's Sales, Solutions Engineering, Support, and Product teams. Your success will be measured by gross and net revenue retention, churn reduction, and growing your book of business by 10–15% in additional annual revenue. You'll also carry a smaller new business sales quota.

What You’ll Do

Account Management, Retention & Expansion

- Own a book of SMB and mid-market client accounts, serving as their primary relationship manager.
- Drive renewals and reduce churn by staying close to client goals, product usage, and satisfaction.

- Lead pricing, renewal, and contract conversations, partnering with leadership on approvals.
- Monitor account health and usage to identify risks and expansion opportunities early.

- Grow your book of business by 10–15% in additional annual revenue through upsells, volume upgrades, new use cases, and add-on products.

New Business Sales & Onboarding

- Handle inbound demo and meeting requests from SMB and mid-market prospects.
- Run discovery calls and product demos, and close new SMB and mid-market business.

- Onboard new SMB and mid-market clients, ensuring they're set up and successful on the platform.





Cross-Functional Collaboration & Operations

- Coordinate with Solutions Engineering, Support, and Product to resolve client needs quickly.

- Bring client feedback to the Product team to help shape the roadmap.
- Keep account activity, pipeline, and renewal forecasts up to date in the CRM.
- Help build playbooks and processes for a scalable account management function.

About You

- 2+ years of experience in account management, customer success, or sales at a B2B SaaS company.
- Demonstrated track record of owning renewals and achieving retention and expansion targets.
- Comfortable leading pricing, renewal, and contract conversations with clients.

- Experience running product demos and moving prospects through a sales cycle.
- Strong organizational skills and follow-through across a large portfolio of accounts.
- Clear, confident communicator who builds trust quickly with clients.

Bonus

- Experience managing enterprise accounts alongside a high volume of SMB and mid-market clients.
- Experience onboarding clients onto a SaaS platform.
- Familiarity with workflow automation, form-building, or data platforms.

- Experience with HubSpot or a similar CRM.
- Experience working at a high-growth startup.

What We Offer

- Competitive compensation and equity
- Health, dental, and vision coverage

- Unlimited PTO

- Downtown Toronto office location
- Office snacks and monthly catered lunch
- A supportive, low-ego team that values ownership and growth
- Company offsite to connect and recharge

Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.

📌 SMB / Mid-Market Account Manager (Toronto)
🏢 Feathery
📍 Toronto