Procurement & Program Manager – Digital Strategy RFP to lead vendor selection for an enterprise-wide Digital Strategy using strategic sourcing and weighted evaluation

S I Systems; Toronto; Hybrid; CAD 110,000 - 160,000; Part time

Job summary

S.I. Systems Ltd. seeks a Procurement & Program Manager to lead a Digital Strategy RFP for enterprise-wide vendor selection. The role covers requirements, evaluations, executive recommendations and contract award, with a 4–6 month contract starting in 2027 in Mississauga, Ontario.

The incumbent will manage up to 16 vendors, oversee weighted evaluations and drive commercial negotiations, including TCO comparisons and transition planning, in a hybrid working environment.

Qualifications

• 8+ years in strategic sourcing, technology procurement or enterprise program management.
• Ownership of large, complex competitive RFPs from requirements through award and contracting.
• Multi-vendor sourcing with executive-level presentations across C-suite and stakeholders.
• TCO modeling, commercial analysis, rate-card normalization and negotiation.
• Digital transformation domain familiarity spanning CX, web/app architectures, cloud, data/AI and operating-model redesign.
• Legal authorization to work in Canada for the full contract term.

Responsibilities

• Define objectives, scope, requirements and deliverables with Digital, Marketing, IT, Data, Finance, Operations, Legal and Procurement leaders.
• Administer weighted evaluations covering domain expertise, solution feasibility, team quality, commercials and cultural fit.
• Coordinate communications for up to 16 vendors, including NDAs, information distribution and Q&A.
• Orchestrate longlist qualification, shortlist scoring, finalist presentations, workshops and reference checks.
• Prepare executive briefings, recommendations, risk mitigation plans and SteerCo/C-suite decision materials.
• Lead commercial negotiations and contract award activities, including TCO comparisons, pricing normalization, BAFO discussions, contract markups and transition handoff.
• Maintain the master RFP plan, decision log, risk register, vendor tracker, evaluator schedule, executive status reporting and auditable procurement records.

Skills

Strategic sourcing

Technology procurement

Enterprise program management

Multi-vendor sourcing

TCO modeling

Digital transformation

Executive presentations

Contract negotiations

Education

Bachelor’s degree in Business, Supply Chain, Information Systems or related field

Master’s degree or MBA preferred

PMP, CPSM or CIPS certification

Job description

Procurement & Program Manager – Digital Strategy RFP to lead vendor selection for an enterprise-wide Digital Strategy using strategic sourcing and weighted evaluation

Our enterprise client is seeking a Procurement & Program Manager – Digital Strategy RFP to lead vendor selection for an enterprise-wide Digital Strategy using strategic sourcing and weighted evaluation

Lead a competitive RFP involving up to 16 consulting and digital agency vendors to select a partner for an enterprise-wide Digital Strategy. Supporting the Strategic Procurement lead, this role spans requirements, evaluations, executive recommendations, commercial negotiations and contract award. The contract is expected to run 4–6 months, with a target start in 2027.

Must Haves

• 8+ years in strategic sourcing, technology procurement or enterprise program management; ownership of large, complex competitive RFPs from requirements through award and contracting, with procurement governance and audit-trail discipline.
• Multi-vendor sourcing, high-volume supplier communications and executive-level presentations across C-suite, VP and cross-functional stakeholder groups.
• TCO modeling, commercial analysis, rate-card normalization and negotiation.
• Digital transformation domain familiarity spanning customer experience, web/app architectures, cloud, data/AI, omni-channel and operating-model redesign.
• Legal authorization to work in Canada for the full contract term.

Nice to Have

• Financial services, capital markets, exchange, regulated enterprise or similarly complex procurement background.
• Sourcing global management consultancies, technology integrators and boutique digital agencies within the same competition.
• Formal SteerCo governance, reference checks, vendor debriefs and implementation transition planning.
• PMP, CPSM or CIPS certification.
• Bachelor’s degree in Business, Supply Chain, Information Systems or a related field; Master’s degree or MBA preferred.

Responsibilities

• Define objectives, scope, requirements and deliverables with Digital, Marketing, IT, Data, Finance, Operations, Legal and Procurement leaders.
• Administer weighted evaluations covering domain expertise, solution feasibility, team quality, commercials and cultural fit, including evaluator training, scoring normalization and debriefs.
• Coordinate communications for up to 16 vendors, including NDAs, information distribution, briefing logistics and controlled, anonymized Q&A.
• Orchestrate longlist qualification, shortlist scoring, finalist presentations, workshops and reference checks.
• Prepare executive briefings, recommendations, risk mitigation plans and SteerCo/C-suite decision materials.
• Lead commercial negotiations and contract award activities, including TCO comparisons, pricing normalization, BAFO discussions, contract markups and transition handoff.
• Maintain the master RFP plan, decision log, risk register, vendor tracker, evaluator schedule, executive status reporting and fair, auditable procurement records.

Our enterprise client is seeking a Procurement & Program Manager – Digital Strategy RFP to lead vendor selection for an enterprise-wide Digital Strategy using strategic sourcing and weighted evaluation

Lead a competitive RFP involving up to 16 consulting and digital agency vendors to select a partner for an enterprise-wide Digital Strategy. Supporting the Strategic Procurement lead, this role spans requirements, evaluations, executive recommendations, commercial negotiations and contract award. The contract is expected to run 4–6 months, with a target start in 2027.

Contract, Mississauga, Hybrid, Working Hours: EST

Must Haves

• 8+ years in strategic sourcing, technology procurement or enterprise program management; ownership of large, complex competitive RFPs from requirements through award and contracting, with procurement governance and audit-trail discipline.
• Multi-vendor sourcing, high-volume supplier communications and executive-level presentations across C-suite, VP and cross-functional stakeholder groups.
• TCO modeling, commercial analysis, rate-card normalization and negotiation.
• Digital transformation domain familiarity spanning customer experience, web/app architectures, cloud, data/AI, omni-channel and operating-model redesign.
• Legal authorization to work in Canada for the full contract term.

Nice to Have

• Financial services, capital markets, exchange, regulated enterprise or similarly complex procurement background.
• Sourcing global management consultancies, technology integrators and boutique digital agencies within the same competition.
• Formal SteerCo governance, reference checks, vendor debriefs and implementation transition planning.
• PMP, CPSM or CIPS certification.
• Bachelor’s degree in Business, Supply Chain, Information Systems or a related field; Master’s degree or MBA preferred.

Responsibilities

• Define objectives, scope, requirements and deliverables with Digital, Marketing, IT, Data, Finance, Operations, Legal and Procurement leaders.
• Administer weighted evaluations covering domain expertise, solution feasibility, team quality, commercials and cultural fit, including evaluator training, scoring normalization and debriefs.
• Coordinate communications for up to 16 vendors, including NDAs, information distribution, briefing logistics and controlled, anonymized Q&A.
• Orchestrate longlist qualification, shortlist scoring, finalist presentations, workshops and reference checks.
• Prepare executive briefings, recommendations, risk mitigation plans and SteerCo/C-suite decision materials.
• Lead commercial negotiations and contract award activities, including TCO comparisons, pricing normalization, BAFO discussions, contract markups and transition handoff.
• Maintain the master RFP plan, decision log, risk register, vendor tracker, evaluator schedule, executive status reporting and fair, auditable procurement records.

Disclaimer:

AI may be used in evaluating candidates.

This posting is for an existing vacancy.