Principal Proposal Manager (Bilingual)

Softchoice; Ottawa; On-site; CAD 91,000 - 114,000; Full time

Benefits offered by this job

Health and Wellbeing benefits

RRSP/DPSP retirement plan with company

Paid time off & holidays

Employee discount program

Job summary

Softchoice is seeking a Principal Proposal Manager (Bilingual) to lead the strategy and execution of its most complex, high‑value opportunities. You will guide cross‑functional teams, shape proposals and pricing, and protect margin across multi‑million‑dollar bids.

With 7–10 years in pursuit management and a fully bilingual capability, you’ll ensure compliant, differentiated responses that win while aligning with executive priorities.

Qualifications

• 7-10 years of progressively senior proposal, capture or pursuit management experience.
• Fully bilingual in English & French (both written & spoken) required.
• Exceptional writing, editing and visual design skills.

Responsibilities

• Lead the full lifecycle of large, complex enterprise pursuits from qualification through proposal submission and negotiation support.
• Direct cross-functional pursuit teams and governance to deliver compliant, persuasive proposals.
• Develop win strategies, pricing approaches and risk mitigation in collaboration with Sales, Legal, Finance and partners.
• Ensure executive alignment and a credible path to profitable growth.

Skills

APMP certification

Bilingual English & French

Executive writing & editing

Proposal leadership

Education

Bachelor’s degree

Job description

Principal Proposal Manager (Bilingual)

Date: Nov 9, 2026

Location: Toronto, ON, CA • Nova Scotia, CA • New Brunswick, CA • Ottawa, ON, CA

Company: Softchoice

Why you’ll love Softchoice:

At Softchoice, a World Wide Technology (WWT) company, we work together to make a new world happen. As an IT solutions provider serving U.S. commercial and SMB organizations, as well as the entire Canadian market, we help organizations turn ambition into real‑world outcomes. We do this through the delivery of secure cloud, AI, software and digital workplace solutions that enable agility, innovation and growth.

With a highly engaged, high-performing team, we are certified as a Great Place to Work® in both Canada and the United States, and have been recognized as a Best Workplace in Canada for more than 20 years. We stand proudly for our people and their success through career development and advancement, and continuously strive to do what’s good for our people and communities.

As part of WWT, we connect customers to the global scale, advanced innovation, world‑class partnerships, and deep expertise of a leader in AI and digital transformation. This includes access to WWT’s Advanced Technology Center (ATC), a collaborative ecosystem featuring state‑of‑the‑art hardware and software that enables customers and partners to conceptualize, test, and validate innovative solutions before deploying them at scale.

The impact you will have:

The Principal Proposal Manager is an enterprise pursuit leader who owns the strategy and execution of the organization’s most complex, high‑value opportunities. From qualification and capture planning through proposal submission, negotiation support and lessons learned, this role directs cross‑functional pursuit teams to produce differentiated, commercially sound proposals that strengthen win probability, protect margin and advance the strategic plan.

The Principal Proposal Manager leads a portfolio of five to six large (multi‑million dollar), strategic pursuits at various stages of development. As the pursuit strategist and senior lead, this role establishes governance, directs the response strategy, challenges assumptions and aligns executive sponsors, Sales, solution teams, pricing, Finance, Legal and external partners around a compelling and profitable offer. The role is accountable for maintaining momentum, resolving critical issues and ensuring that every submission reflects a clear customer value proposition, disciplined commercial judgment and a credible path to profitable growth.

As a trusted advisor to senior Sales and business leaders, this role maintains executive alignment on the desired outcome, identifies and escalates material risks, and redirects the team when the strategy, solution or commercial position is unlikely to produce a differentiated and profitable result.

What you’ll do:

• Leads the full lifecycle of large, complex, multi‑million‑dollar pursuits following the decision to bid, translating the capture strategy into a disciplined proposal plan, governance model and executive review cadence. Directs internal and external contributors, resolves cross‑functional dependencies, and maintains accountability for strategy, quality, compliance, schedule, risk and commercial outcomes.

• This requires coordination of internal and external resources as required.

• Seeks to have a good understanding of (internal and external) customers’ needs and has the skills necessary to help (internal and external) customers understand business challenges.

• Owns the timely delivery of compliant, persuasive and commercially viable proposals that clearly differentiate Softchoice, improve win probability and protect the margin position.

• Leads the team effort. Excellent project management skills necessary.

• Leads the pursuit team in developing and validating the win strategy, including competitive positioning, value proposition, solution architecture, delivery approach, proof points, pricing strategy and risk posture. Ensures that all proposal elements reinforce the agreed strategy and that material trade‑offs are presented to executive stakeholders for timely decisions.

• Strategic decisions and execution required.

• Creates pricing strategies with Sales stakeholders.

• Provides experience‑based guidance for response direction.

• Leads early identification and ongoing management of contractual, financial, delivery, solution and compliance risks. Partners with Legal, Finance, Sales and solution leaders to evaluate exposure, develop mitigation strategies and elevate material issues before commitments are made.

• Works with legal department to review terms and conditions.

• Shapes the executive narrative for each pursuit, translating customer priorities, solution value, differentiation, proof points and commercial rationale into persuasive executive summaries and proposal content tailored to the customer’s evaluation criteria and decision drivers.

• Utilizes RFP content tools to support content creation.

• Leads the pursuit through shortlist activities, presentations, clarifications, best‑and‑final offers and negotiation support, preserving strategic consistency and commercial discipline as the offer evolves.

• Follows up requests like BAFOs or Clarifications

• Anticipates business, resource and execution issues that could compromise the pursuit and leads cross‑functional resolution. Escalates material decisions with clear options, implications and recommendations, and responds to stakeholders with the accuracy, urgency and judgment expected of a senior pursuit leader.

What you’ll bring to the table:

• 7-10 years of progressively senior proposal, capture or pursuit management experience, including leadership of complex, multi‑million‑dollar enterprise opportunities and cross‑functional pursuit teams (full cycle proposal management experience).

• IT experience required.

• APMP certification or the ability to get certification within 1 year of employment is required.

• Proven record of leading complex, high‑value pursuits and improving business outcomes through strong qualification, differentiated win strategies, disciplined pricing, risk management, margin protection and demonstrated win performance.

• Exceptional writing, editing and visual design skills, with strong attention to detail and compliance.

• Advanced pursuit and program leadership skills, including the ability to establish governance, manage multiple concurrent strategic proposals, facilitate executive decisions, resolve cross‑functional conflict and recover pursuits at risk under tight deadlines.

• Proficiency in proposal management and AI tools (RFP‑A, Claude, Co‑Pilot, etc.)

• Exceptional executive communication, facilitation and influencing skills, with the credibility to challenge assumptions, align diverse senior stakeholders and drive timely decisions across Sales, Finance, Legal, delivery, solution and partner teams.

• Fully bilingual in English & French (both written & spoken) required.

• Bachelor’s degree

Compensation:

A reasonable estimate of the current base pay range for this position in Canada is $91,000 to $114,000, annually + 12% as target incentives.

Actual salary will be based on a variety of factors, including location, experience, skill set, education, and related certification. The range for this position in other geographic locations may differ.

Softchoice offers a comprehensive and competitive benefit plan to all full‑time employees, which includes:

• Health and Wellbeing: Medical and Dental Care, Employee & Family Assistance Program

• Financial Benefits: RRSP/DPSP Retirement Savings Plan with Company Matching, Life and Disability Insurance

• Paid Time Off: Vacation and Sick Leave, Holidays, Parental Leave, Volunteer Days, Bereavement Leave

• Additional Perks: Employee Discount Program

Why You’ll Love Working Here:

• The People: You’ll thrive in our collaborative environment, surrounded by incredible colleagues who foster support and innovation, driving our collective success

• High-Performing Culture: At Softchoice, we are dedicated to achieving our goals and committed to success for our customers and each other

• Flexibility: Plan your workdays in a way that suits you best

• Award-Winning Workplace: Proudly recognized as a Great Place to Work for 21 consecutive years

• Inclusive Culture: We are committed to a company culture where every team member can be their authentic self

• Competitive Benefits: Benefit from competitive perks that start on day one

Inclusion & Equal opportunity employment:

We are an equal opportunity employer committed to diversity, inclusion & belonging . People seeking employment at Softchoice are considered without regard to any protected category including but not limited to, race, color, religion, national origin, age, sex, marital status, ancestry, disability, veteran status, gender identity, or sexual orientation.

Require accommodation? We are ready to help:

We are proud to provide interview & employment accommodation during the recruitment and hiring process. If you require any accommodation to apply or interview for a position, please reach out directly to [e-mail] . We are committed to working with you to best meet your needs.

Our commitment to your experience:

We are committed to the safety of all applicants and team members. With that in mind, we have implemented digital interviewing for everyone. We understand that you may need to interview with distractions around you (such as children or furry friends) and we will be doing the same.

Before you start with us, we will conduct a criminal record check, verify your education, and check your references.

When you join Softchoice, we will onboard you remotely. Don't worry. It's quick, simple and you'll be connected with your new team in no time.

EoE/M/F/Vet/Disability