A Bit About Us Arlo is a world-leading SaaS company on a mission to revolutionize professional training. With customers in over 70 countries, over 7.5M people trained, and $3B in course transactions, Arlo is loved by thousands of trainers and millions of learners worldwide. Arlo’s all-in-one training management platform handles everything from course creation and scheduling to delivery and operations.

Arlo is a world-leading SaaS company on a mission to revolutionize professional training. With customers in over 70 countries, over 7.5M people trained, and $3B in course transactions, Arlo is loved by thousands of trainers and millions of learners worldwide. Arlo’s all-in-one training management platform handles everything from course creation and scheduling to delivery and operations.

We believe human connection is at the heart of great learning. By blending that philosophy with the latest in AI and e-learning technology, Arlo helps training providers save time, grow revenue, and deliver exceptional learning at scale. Here, you’ll find a supportive team that trusts you to make an impact, gives you the freedom to grow, and the space to do your best work.

We value clarity, ownership, and curiosity, and we’re not afraid to challenge ideas to reach the best outcome. We work hard, move quick, and celebrate wins together. This role is a key part of Arlo’s next phase of growth.

Global expansion, deepening our AI capabilities, and empowering a passionate community of training professionals shaping the future of learning.

What you’ll do As Senior Sales Executive, you carry the largest individual quota on the North America team and operate at a different level of deal complexity, strategic input, and market ownership. You personally close enterprise deals, help shape the regional go-to-market strategy, and drive the outbound motion that supports it.

North America is Arlo’s most significant growth opportunity, and this role won’t inherit a built machine - you’ll help build it. That calls for someone comfortable with both the discipline of execution and the ambiguity of a market that’s still taking shape.

The role doesn’t carry direct reports. It carries a bigger mandate and a harder set of deals instead. The Head of Sales remains accountable for the overall regional number; this role is accountable for the largest individual contribution to it.

Responsibilities Personal Quota &

- Sales Execution Achieve your individual MRR target each quarter





Close new business across the full deal range, with a specific mandate to close deals above $1,500 MRR (NZD) that require complex commercial selling.

Maintain a personal pipeline that provides sustainable quarterly and annual coverage, at minimum 2× quota in qualified open deals at all times

Provide accurate monthly and quarterly forecasts and pipeline reporting to the Head of Sales

GTM Strategy &

- Market Input Help translate the global sales strategy into a North America execution plan, covering target segments, outreach channels, messaging priorities

Develop and maintain a point of view on segment prioritisation for North America - which verticals, deal sizes, and use cases to focus on, and why - informed by your direct market experience

Provide ongoing intelligence to the Head of Sales on competitive dynamics, buyer behaviour, and market conditions affecting the regional strategy

Partner with the Head of Marketing and Head of Product on GTM alignment, contributing to joint planning as a senior voice from the field

Represent the voice of the North American buyer internally, sharing how prospects actually evaluate, object, and decide in this market

Enterprise &

- Large Deal Leadership Personally lead and close complex, multi-stakeholder deals, including RFPs, enterprise contracts, and opportunities with extended evaluation cycles

Serve as the senior commercial lead on the region’s highest-value opportunities, setting the approach, managing stakeholders, and driving to close

Build and maintain direct relationships with senior decision-makers (C-level and VP-level) at target accounts

Identify accounts with significant expansion potential and build a structured long-term engagement plans

Feed market and customer signals back to Product, surfacing patterns from buyer conversations, objections, and loss reasons that should inform product direction

Represent Arlo at major North American industry events

Outbound Motion Ownership Adapt and execute the global outbound process within North America, tailoring approach, messaging,



and sequencing to fit local procurement practice and buyer behaviour

Align with the SDR on outbound priorities and sequencing quality

Drive a measurable increase in outbound-sourced pipeline as a proportion of your own total pipeline

Develop a partner and referral channel in North America that supplements direct outbound and inbound activity

Process &

- Tool Ownership Take ownership of at least one defined sales process or tool, leading its implementation, adoption, and continuous improvement across the team

Document your process area well enough that it can be handed over or replicated

Contribute to sales process and tooling improvement beyond your own area, escalating friction points with recommendations

Maintain CRM accuracy as standard - pipeline stage, MRR estimates, close dates, and activity logs

Provide mentorship to other sales team members on enterprise deal management and commercial negotiation

Experience &

- Capabilities Experience Prior experience in a senior individual contributor or sales leadership role in B2B SaaS - has operated above the level of a standard quota-carrying AE

Demonstrated track record of closing enterprise or complex deals: multi-stakeholder, extended evaluation cycles, deals equivalent to $1,500+ MRR (NZD)

Proven ability to build or contribute meaningfully to an outbound motion

Experience contributing to GTM strategy alongside direct sales execution

Has led commercial conversations at C-level - pricing, contract terms, and procurement navigation

Skills &

Qualifications Strong commercial acumen - can structure, negotiate, and close complex agreements

Excellent communication and presentation skills at executive level

Analytical capability - can translate pipeline data and market trends into actionable insight

Degree qualification preferred but not essential

Capabilities Comfortable in a scale-up environment where change is constant and innovation and collaboration are essential

Moves fluidly between deal-level execution and market-level strategy without losing rigour in either

Comfortable with ambiguity, and able to set a direction in a market that doesn’t yet have a complete playbook

Builds credibility quickly with senior buyers

Challenges assumptions in how the market is approached, how deals are run, and how the team operates

Reads data and acts on it, using pipeline and performance metrics to drive decisions rather than just report on them

📌 Senior Sales Executive (Toronto)
🏢 Arlo Training Management Software
📍 Toronto