Lead Account Executive & Sales Manager

Origin; Canada; Remote; CAD 80,000 - 120,000; Full time

Job summary

A fast-paced startup in Canada seeks a hands-on Lead AE & Sales Manager to drive pipeline generation and deal execution. This high-impact role involves optimizing sales processes and coaching an SDR team. The position offers a clear path to senior leadership as the company scales, with a focus on data-driven execution and refining sales playbooks.

Benefits

Meaningful equity package

Unlimited PTO

Wellness stipend

Mental wellness program

Flexible hours

Qualifications

• 3+ years of experience as an SDR or equivalent in outbound sales.
• 3-5 years of Enterprise AE experience selling complex deals.

Responsibilities

• Drive pipeline generation strategy and optimize sales processes.
• Manage a high-performing SDR team and ensure seamless handoff.
• Own pipeline reporting and establish conversion benchmarks.

Skills

Coaching

Sales Playbooks

Data Analysis

Outbound Prospecting

Tools

Salesforce

Sales Engagement Tools

Job description

Origin is reimagining wealth management by making it accessible and affordable to all.

Today, money is the #1 source of stress - more than jobs, health, and relationships combined. That stress is exacerbated in the current economic environment, which is presenting people with once-in-a-generation financial challenges. Origin is tackling this problem head on by expanding access to financial planning for those who have historically been boxed out due to high barriers to entry.

Our product simplifies finances for individuals making it easy to manage spend and investments, get expert advice, and take action to hit financial goals.

We are a fast-paced startup in the series B round, led by repeat founders and backed by leading VC firms like Founders Fund, Felicis, and General Catalyst.

THE ROLE

Mission

Origin is looking for a hands-on Lead AE & Sales Manager to drive both pipeline generation and deal execution. You’ll be the sole AE (for now) while managing our SDR function through the SDR Team Lead. This is a high-impact role that requires balancing strategic thinking with execution—refining playbooks, improving deal progression, and ensuring we hit sales targets.

Responsibilities

Own Pipeline Generation & Quota Execution

• Drive pipeline generation strategy, ensuring SDRs source 20-30% of total pipeline.
• Own AE quota performance, ensuring deals progress through the pipeline efficiently.
• Optimize the end-to-end sales process, refining playbooks, qualification frameworks, and outbound execution.
• Diagnose pipeline gaps and implement corrective actions to increase conversion rates.

Refine & Improve SDR & Sales Playbooks

• Develop, implement, and refine Sales Playbooks and Account Plans to improve deal conversion.
• Optimize multi-threading, outreach sequences, and qualification strategies.
• Ensure alignment between SDR prospecting and AE deal execution.

Coach & Lead the SDR Function

• Manage a high-performing SDR team while ensuring seamless SDR-to-AE handoff.
• Provide structured coaching, call reviews, and real-time deal support.

Drive Data-Driven Execution

• Own pipeline reporting, forecasting, and deal inspection to track performance.
• Establish conversion benchmarks from activity → SQOs → Closed Deals and refine as needed.
• Maintain Salesforce accuracy to provide full visibility into deal progress and next steps.

Must Have

• 3+ years of experience as an SDR (or equivalent in outbound sales, pipeline generation, or prospecting).
• 3-5 years of Enterprise AE experience, selling complex, multi-stakeholder deals in the 6-7 figure range.
• Proven success in multi-threading and prospecting into executive buyers (HR, Finance, Total Rewards, Procurement).
• Strong track record in building, refining, and executing sales playbooks.
• Deep understanding of outbound prospecting, pipeline inspection, and deal conversion.
• Proven ability to coach SDRs and AEs to improve sales execution.
• Proficiency in Salesforce, sales engagement tools (Outreach, Salesloft, etc.), and data analysis.

Nice-to-Have

• Experience managing SDRs & AEs at a Series A/B startup or fast-scaling SaaS company.
• Familiarity with B2B fintech or financial services sales.
• Experience working cross-functionally with Marketing, Partnerships, and RevOps.

What success looks like

• SDR-sourced pipeline consistently meets or exceeds 20-30% target.
• AE team meets or exceeds quota
• Sales playbooks and outbound processes are continuously refined to improve conversion rates.
• Data-driven decision-making improves pipeline efficiency and forecasting accuracy.

Career Growth and Development

This role offers a clear path to a senior leadership position as we scale. You'll shape the foundation of our go-to-market strategy, and future AE hires will build on your playbooks and processes. Whether you want to grow into a formal leadership role or stay in a high-impact IC, this role is built to flex with your goals.

Eligibility Requirements

• Candidates must be legally authorized to work in the United States or Canada.
• Origin does not sponsor visas.

WHAT WE OFFER

• Meaningful equity package
• Retirement 401k for USA-based Originals

Healthcare and wellness programs:

• Wellness stipend
• Mental wellness program
• Unlimited access to financial planning
• Life insurance for USA-based Originals

Work-life balance:

• Unlimited PTO
• Remote-first culture
• Flexible hours (Core hours: 9 AM to 5 PM local time)
• Parenthood and fertility assistance
• Monthly co-working membership reimbursement
• English tutoring stipend for International Originals
• Build your home-office one-time stipend
• Pick your setup (Apple, Windows) and accessories

ORIGINALS

Fulfilling our mission is only possible with a diverse team that breathes for excellence and is hugely committed to making money simple for everyone, everywhere.

As a team, we are obsessed with delivering the best solution possible to our members through an elegant and self-guided experience. We know that building a product of this magnitude requires from us tons of creativity, autonomy, and flexibility to move fast and embrace uncertainties with ownership. This is who we daily pursue to be!

To embrace talented people like this and provide the necessary resources to achieve their best versions, we believe in the power of a healthy environment where each person is valued for who they are and have clear goals and expectations for the future they can build within the company. Each person here is seen as a key player in our team.

Our environment is diverse, with excellent people and equal opportunities. We believe in the power of the individuality and uniqueness of each of us to make our team even more powerful.

We are building an outstanding solution, and here is an invitation for you to become an Original and join us on this journey!