Senior Account Executive

OnePlan; Toronto; Remote; CAD 100,000 - 125,000; Full time

Job summary

A leading technology company seeks a Senior Account Executive to manage a full sales cycle for enterprise accounts. This remote position involves working closely with C-suite executives to address their needs with tailored solutions. The ideal candidate will have experience in selling SaaS or Microsoft ecosystem solutions, confidence in engaging senior stakeholders, and a consultative approach. A solid understanding of sales methodologies is a bonus. Comprehensive health benefits and a collaborative environment are offered.

Benefits

Comprehensive health, dental, and vision benefits

Employer RRSP and 401K matching

Collaborative and diverse environment

Qualifications

• Experience selling SaaS or Microsoft ecosystem solutions into large enterprise accounts.
• Ability to manage long, complex sales cycles with multiple stakeholders.
• Strong communication and relationship-building skills.

Responsibilities

• Manage the full sales cycle from prospecting to close for enterprise accounts.
• Deliver tailored demos and lead technical discovery.
• Identify upsell and cross-sell opportunities within existing accounts.

Skills

Experience selling SaaS

Consultative approach

Confidence engaging C-suite

Sales methodologies familiarity

Ownership mindset

Tools

Salesforce

Job description

Senior Account Executive

Department: Sales

Employment Type: Permanent - Full Time

Location: Canada (Remote)

Description

At OnePlan, we specialize in creating AI-enabled solutions that make strategic portfolio, financial, resource, and work management seamless. We help businesses bridge the gap between strategy and execution by offering solutions that boost business agility, streamline project management, and optimize resources.

What Makes Us Unique?

What truly makes OnePlan stand out is our commitment to delivering powerful solutions and fostering a culture of collaboration. We combine robust analytics with a platform that integrates seamlessly into the tools businesses already know and trust. Our high‑trust, team‑focused environment allows us to innovate quickly and deliver solutions that drive meaningful results for our clients. We're passionate about exceeding expectations, working together to empower organizations to succeed in a rapidly changing business landscape.

About the Role

This is a strategic sales role where you’ll own your business end to end. You’ll work closely with enterprise prospects, dig into their business challenges, and guide them toward solutions that make sense for where they are and where they want to go. If you’re someone who is comfortable in complex sales cycles, enjoys consultative conversations, and thrives with a lot of autonomy, you’ll feel right at home here.

What You’ll Do at OnePlan

• Manage the full sales cycle from prospecting to close for enterprise accounts
• Work directly with C‑suite and senior leaders to understand their goals and map OnePlan’s solutions to their priorities
• Deliver tailored demos and lead technical discovery alongside our Solution Consultants
• Build and configure use cases and guide customers through pilots and trial
• Create territory plans and account strategies that support a strong, healthy pipeline
• Build trusted relationships with prospects, partners, and internal teams
• Prepare and negotiate pricing, SOWs, and contract terms
• Maintain accurate pipeline and forecasts in Salesforce
• Work closely with Customer Success and Product to ensure smooth handoffs and long‑term customer value
• Identify upsell and cross‑sell opportunities within existing accounts
• Stay plugged into industry trends, Microsoft ecosystem programs, and competitive movements

Our Ideal Fit

• Experience selling SaaS or Microsoft ecosystem solutions into large enterprise accounts
• Comfort managing long, complex sales cycles with multiple stakeholders
• A consultative approach that builds trust and keeps conversations grounded
• Confidence engaging C‑suite and senior leaders on strategic business outcomes
• Familiarity with sales methodologies such as MEDDPICC, Challenger, or Sandler
• Experience partnering with Solution Consultants or presales teams to shape deals
• Ability to guide customers through pilots, use cases, and early solution validation
• Strong ownership mindset with steady communication and follow through

Bonus Points if You Have

• Experience selling PPM, work management, or planning software
• Understanding of Microsoft’s co‑sell programs and partner ecosystem
• Exposure to global enterprise environments or long‑cycle strategic sales
• Comfort configuring product scenarios or hands‑on demos

More Reasons Why You Should Apply!

• We’re a remote‑first company with team members across the USA, Canada, UK, and India!
• OnePlan has been recognized as the Global Microsoft Partner of the Year in Project and Portfolio Management in 2019, 2020, 2021, and 2022.
• We’ve been named a "Strong Performer" in the latest Forrester Strategic Portfolio Management WAVE report.
• We offer comprehensive health, dental, and vision benefits, with additional insurance options.
• Employer RRSP and 401K matching programs.
• A fun, collaborative, and diverse environment with regular health and team challenges to keep things light and enjoyable!

At OnePlan, we are committed to equal employment opportunities regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or veteran status. We are proud to be an equal‑opportunity workplace.

Upon receipt of an offer letter, candidates will be subject to a standard background check process. Disclaimer: We’ll only contact candidates who have applied directly through our official channels. Any communication about job offers will always come from an email address linked to OnePlan Solutions, and we’ll follow our standard hiring process every time. You’ll never be asked for money or personal information during the interview process. If something feels off, don’t hesitate to reach out to us to confirm.

Ready to Apply? Check out what it’s like to work at OnePlan and learn more about us at https://oneplan.ai/