Executive Engineering Jobs in Ontario (NOW HIRING)

Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.

We're looking for an Account Executive to join our rapidly growing Sales team, with a specific focus on VoIP and unified communications. This is a specialized track within our Sales team dedicated to understanding how law firms run their phone and messaging systems today and helping them modernize that setup, layered on top of the core Account Executive skill set.

This role is for someone with a positive attitude, growth mindset, and a sense of ownership to take a sales motion from early-stage to repeatable. As a confident communicator who can translate technical concepts - call routing, number porting, network readiness - into business value for non-technical buyers, you'll own the full sales cycle for this offering across both net-new prospects and our existing customer base, with a focus on our SMB business. You'll partner cross-functionally with Account Executives, Customer Success, Solutions Engineering, and Onboarding/Migrations teams to bring VoIP/telephony expertise into their conversations and handoffs.

Our Sales team connects law firms with the technology they need to run their practice. This role adds a dedicated VoIP/telephony motion to that team - supporting and driving adoption of the Voice & Messaging pillar of Clio's Unified Communications initiative, which brings voice, messaging, and email into a single, consistent experience across the Clio product suite. You'll own a defined book of your own, while also acting as the specialist other Account Executives and Customer Success Managers turn to when they need help building the case with their accounts.

• Own the complete sales process end to end - qualification, discovery, demo, business case, proposal, negotiation, and close - across both net-new prospects and existing customer accounts.

• Sell to firm owners, managing partners, office administrators, and IT decision makers, navigating multiple stakeholders to build consensus and secure approvals.

• Run trials as real opportunities on a real close plan, driving trial-to-paid conversion and time-to-activation.

• Drive attach and expansion within our existing customer base, identifying firms whose current phone setup is a fit and building the cross-sell case alongside their Customer Success Manager or Account Manager.

• Maintain an accurate 3x qualified pipeline spanning new-business and expansion opportunities, and forecast with precision in Salesforce.

• Consistently meet and exceed monthly and quarterly targets across seats, trials, and revenue, across both new and existing accounts.

• Qualify the firm's current communications environment - incumbent provider, contract end date, seat and user counts, DID and toll-free inventory, and monthly spend.

• Map the firm's call flows - main line handling, auto attendants and IVR trees, extensions, hunt groups, voicemail routing, and after-hours coverage - and translate them into a working configuration.

• Qualify network and hardware readiness, and scope number porting honestly: LOA and CSR requirements, realistic timelines, common rejection reasons, and what the firm experiences on cutover day.

• Handle the contract-overlap objection credibly, and stay conversant in the realities of this category - E911 and dispatchable location, call-recording consent, and messaging compliance.

• Become the resident expert on the VoIP/UCaaS offering - voice, messaging, call routing, and the integration across our core platform.

• Deliver live demos and needs-based presentations that connect telephony capability to how a law firm actually runs a matter from intake to invoice.

• Act as the voice expert for Account Executives and Customer Success Managers - joining their calls, building the business case with them, and leading the technical portions of the conversation.

• Partner closely with Solutions Engineering on complex configurations, and with Onboarding and Migrations teams to hand off a deal cleanly into cutover - flagging porting risk, hardware needs, and timeline expectations before they become someone else's problem.

• Know when to escalate rather than improvise.

What you may have

• 3+ years of quota-carrying B2B sales experience with a documented record of consistently meeting and exceeding target, ideally spanning both new-business and expansion/cross-sell motions.

• Direct experience selling UCaaS, VoIP, CCaaS, or telecommunications services or a genuinely transferable background in unified communications or contact center.

• Practical familiarity with how business voice works: call flows and auto attendants, extensions and hunt groups, DIDs and number inventory, voicemail routing, and desk-phone provisioning.

• Hands-on experience with number porting, and the ability to set expectations on it.

• Comfort navigating an incumbent provider, including contract end dates, term overlap, and buyout conversations.

• Comfort in working in an AI-assisted environment.

• Experience selling into an existing customer base - building a case with a champion rather than against an incumbent, and being sensitive to renewal timing and account health.

• Strong discovery and value-based selling instincts, disciplined pipeline management, and accurate forecasting in Salesforce.

• A high tolerance for ambiguity - you'll help build the playbook, not just run it.

• Have direct experience with platforms like RingCentral, Dialpad, Zoom, 8x8, Nextiva, GoTo, Vonage, or a carrier or CLEC.

• Have legal technology, legal services, or professional-services vertical experience.

• Are familiar with the regulatory layer - E911 and dispatchable location, STIR/SHAKEN, A2P messaging registration, and call-recording consent.

• Are comfortable reading basic call-quality diagnostics - jitter, latency, packet loss, MOS - well enough to know whether a problem is ours or the customer's network.

• Have experience partnering with onboarding, implementation, or migrations teams to hand off a technical sale cleanly.

• Are bilingual English/French, or have experience selling into Canada.

What you will find here:

Compensation is one of the main components of Clio's Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.

Some highlights of our Total Rewards program include:

• Competitive, equitable salary with top-tier health benefits, dental, and vision insurance

• Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin and Sydney) to be in office minimum twice per week.

• Flexible time off policy, with an encouraged 20 days off per year.

• $2000 annual counseling benefit

• RRSP matching and RESP contribution

• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years

Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility

Our team shows up as their authentic selves, and are united by our mission. We are dedicated todiversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.

Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.

Learn more about our culture atclio.com/careers

We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions.

Disclaimer: We only communicate with candidates through official @clio.com email addresses.