Senior Account Executive (Toronto)

ABOUT CINCHY

Cinchy is a Toronto-based, investor-backed enterprise software company. Our flagship platform, PeriMind, is the AI Connectivity & Control Plane purpose-built to govern, manage, and secure autonomous AI agent interactions in real time. Every time an AI agent queries a database, invokes an API, or triggers a workflow, PeriMind authenticates, authorizes, and audits that action instantly.

Trusted by leading institutions, including RBC, TD Bank, Raymond James, iA Financial Group, and Brookfield Properties, PeriMind gives CISOs, Chief AI Officers, and CTOs real-time visibility, hard boundary controls, and cryptographic auditability across their AI ecosystems.

THE OPPORTUNITY

We are looking for a dedicated sales hunter based in Toronto (GTA). In this commercial role, you will drive net-new pipeline through targeted Land-and-Expand and Vertical Penetration strategies across legal, professional, and business services mid-market to lower Enterprise accounts (500–5,000 employees).

This is a pure hunter role. You bring the executive network and industry access; we provide a category-defining product, urgent market tailwinds, and equity upside at a key inflection point.

COMMERCIAL PRINCIPLES

• Voice of the Market: Serve as the critical feedback loop between enterprise prospects and our product engineering team, directly influencing the PeriMind product roadmap based on real-time buyer signals.

• Strategic Playbook Author: Build, test, and refine the repeatable go-to-market playbook, establishing standard sales motions for Vertical Penetration.

• High-Velocity Execution: Own the entire revenue lifecycle from initial contact and discovery to negotiation and closing.

WHAT YOU WILL DO

• Build and execute a high-impact territory plan focused on Land-and-Expand opportunities and Vertical Penetration across in region financial and business services accounts.

• Execute a structured sales methodology to qualify, advance, and close complex, multi-stakeholder enterprise deals with average contract values of $100K–$250K ACV.

• Develop and manage relationships with VAR and MSP partners to source, co-sell, and accelerate pipeline.

• Navigate enterprise buying committees, engaging IT, Legal, Compliance, and the C-suite simultaneously and owning the deal from first meeting to signed order form.

• Engage CISO, Chief AI Officer, and CTO personas with compelling narrative-driven discussions on agentic AI security and compliance.

• Synthesize field insights to act as the primary Voice of the Market, guiding product feature prioritization with product leadership.

• Partner closely with the CEO, CTO, and Customer Solutions team (including dedicated Sales Engineering/Technical Account Management support) on deal strategy, demos, and technical due diligence.

• Represent PeriMind at Toronto (GTA) industry events, relevant industry tech conferences, and partner forums.

WHO THIS ROLE IS NOT

• This is NOT a role for a sales professional who relies on a Solutions Engineer for every call. While you will have dedicated access to a Sales Engineer (SE) and Technical Account Manager (TAM) for deep technical validation and architecture design, you must possess strong Technical Fluency to independently articulate AI architecture, agent control planes, and governance frameworks, leading high-credibility technical conversations directly with CISOs and CTOs.

• This is NOT an account maintenance seat. We are seeking a hunter who thrives on outbound pipeline generation, cold account entry, and accelerating multi-threaded enterprise deal cycles from scratch.

WHAT WE PROVIDE

We back our seller with full executive commitment:

• Direct executive access: CEO and CTO available for strategic deals, executive-to-executive outreach, and customer escalations.

• Pre-sales and demo support: Customer Solutions team (including SE/TAM) joins discovery calls and POCs from the first month.

• Proven product-market fit: RBC, TD Bank, Raymond James, iA Financial, and Brookfield Properties are live customers.

• Sales infrastructure: CRM tooling configured before you start. We will fund the tools you identify as necessary to close business.

• Marketing air cover: Marketing generated leads, case studies, a published threat matrix, regulatory reference materials, and analyst briefing support.

• Equity upside commensurate with the risk

Requirements

WHAT YOU BRING

Required

• 8–12 years of B2B enterprise technology sales experience, with at least 5 years in a closing hunter role.

• Strong Technical Fluency: Ability to confidently discuss AI architecture, agent integrations, and data governance models; you will have SE/TAM support for deep-dive technical validation, but you must be able to lead the initial technical narrative.

• Proven track record of carrying and achieving individual quotas of $1M+ ARR in at least 2 of the last 3 years.

• Experience co-selling with VAR and MSP channel partners; comfort navigating partner-influenced and partner-sourced deals.

• Proficiency with a structured sales qualification methodology; disciplined pipeline management and CRM hygiene.

• Experience managing multi-threaded deals with IT, legal, compliance, and executive stakeholders.

• Proven ability to sell in a startup or early-stage environment where you are building the playbook, not following one.

WHY PERIMIND — THE MARKET MOMENT

Enterprises are rapidly deploying AI agents, but existing permission and security models were built for humans. PeriMind delivers the control plane required to safely govern autonomous AI actions at scale.

With regulatory pressures mounting (EU AI Act, NIST AI standards) and key industries facing unprecedented compliance demands, PeriMind provides immediate, quantifiable control. You won't be creating market demand—you will be delivering the standard solution.

WHAT SUCCESS LOOKS LIKE

30 days

• Product certified — can run a solo PeriMind demo

• ICP, verticals, and buyer personas understood

• CRM configured; first 50 target accounts loaded

• First outbound sequence live

60 days

• 10–15 discovery calls completed

• 3–5 qualified opportunities in CRM

• First multi-stakeholder deal in active motion

• Product feedback loop to CTO established

90 days

• $300K–$500K qualified pipeline built

• First POC or paid pilot in negotiation

• Outbound response rate ≥5%

• GTM playbook v1 delivered

6 & 12 months

• 6M: 1 logo closed; $750K+ pipeline

• 12M: $1.5M pipeline

• 12M: +3 logos closed

• 12M: $1M ARR booked

Benefits

COMPENSATION & BENEFITS

• Base salary: CAD $135,000, depending on experience.

• Variable: 1.0x Base Salary at 100% quota attainment; uncapped with accelerators.

• OTE: 2.0x Base Salary at plan; top performance uncapped.

• Quota: CAD $1,000,000 ARR annually.

• Equity: standard company ESOP

• Benefits: Comprehensive health, dental, and vision coverage.

• Remote-first with in-market Toronto (GTA) with travel expenses covered.

OUR HIRING PROCESS

We run a structured, five-stage process designed to support a strong two-way fit:

• HR Consultant Screen (30 min)

• Hiring Manager Interview (60 min)

• Live Discovery Roleplay (45 min)

• Executive Panel (60 min)

• Reference Checks

• Offer