About the Role

As Sales Manager, Revenue Enablement, you are the operational backbone of the sales team. You track KPIs daily, keep the CRM clean to drive real strategic conversations, own pilots from first meeting to signed contract, and clear the path so reps can sell. You don’t set strategy — you make sure nothing in the company slows the team down.

About CDWare

CDWare is a hyper-growth fleet management software company expanding into new sectors and markets across North America. We develop vertically specialized software for industries where operations are critical.

What You’ll Do

Daily Sales Discipline

• Run a 15-minute daily standup with reps and SDRs; triage every open blocker before it costs half a day
• Maintain a live KPI dashboard visible to the CRO and sales leads at all times
• Track activity volume, pipeline coverage, stage velocity, pilot conversion, and quota attainment pace — daily, not monthly
• Flag early warning signals (low activity, slipping coverage, stalled deals) before they show up in a forecast review
• Bring an accurate KPI summary to every leadership meeting so discussions start on facts, not estimates

CRM Hygiene & Business Intelligence

• Run a daily CRM accuracy sweep: every open deal must have a current stage, value, close date, next step, and solution context
• Push back on reps when data is missing or stale — with urgency, not patience
• Build and enforce CRM input standards so data entry is fast, consistent, and complete
• Translate CRM data into a weekly pipeline summary the CRO can trust and act on
• Escalate persistent data quality issues before they surface in a forecast review

Pilot Program Ownership

• Own every pilot end-to-end: design, launch, in-flight management, outcome review, and conversion to signed contract
• Define scope, success metrics, and go/no-go criteria in writing before launch
• Coordinate product, ops, CS, and legal for a clean start; resolve blockers mid-pilot before momentum is lost
• Lead the outcome review with conversion proposal and updated pricing ready before the meeting starts
• Hand off complete deal summary and scope brief to the delivery team

Cross-Departmental Coordination

• Manage the execution interface between Sales and Product, Marketing, Finance, Legal, Ops, and Customer Success
• Own the pricing approval queue and contract redline queue; keep reps informed without making them chase
• Route product questions same-day; maintain a live FAQ; flag stale content to Marketing
• Run the weekly CS–Sales handoff so expansion signals and references don’t get lost

Gatekeeping & Rep Time Protection

• Intercept and redirect admin requests, internal meeting asks, and data entry tasks away from reps
• Maintain a no-go list of tasks that should never land on a rep; enforce it cross-departmentally
• Reps escalate a blocker once — you own the resolution

RFP & Procurement Monitoring

• Monitor RFP/RFI/RFQ release channels: MERX, SEAO, CanadaBuys, and provincial procurement hubs
• Track pre-release signals (ACANs, letters of intent) to surface bids before they are widely circulated
• Watch contract award announcements for competitive intelligence and renewal targeting
• Brief sales leads and CRO on upcoming bids and procurement calendar milestones

Deal Coordination & Forecasting

• Track every active deal and pilot: status, next step, internal dependency
• Coordinate legal, finance, and ops per deal so reps don’t manage those relationships
• Own proposal and quote workflow: accurate, formatted, on time
• Prepare the weekly pipeline and forecast summary for CRO review — built on clean CRM data, not rep self-reporting

What We’re Looking For

• 4–8 years in revenue operations, sales operations, deal desk, or sales enablement
• Experience in a scaling company where products, team structure, and processes were all evolving at once
• Proven ability to enforce activity discipline and KPI accountability with a sales team — consistently, not just at quarter-end
• Track record of building KPI dashboards that leadership actually uses to make decisions
• Genuine obsession with CRM accuracy and a willingness to push reps to update data when it’s uncomfortable
• Has owned pilot programs end-to-end, not just kicked them off — knows how to keep prospects engaged through the messy middle
• Fluency in sales process from first touch to close, and where deals tend to break
• Clear, direct communicator in both English and French
• Comfortable holding multiple departments accountable simultaneously without formal authority

Nice to Have

• Experience in bilingual government and enterprise procurement environments
• Familiarity with MERX, SEAO, CanadaBuys, or provincial procurement platforms
• Background in solution-selling B2B SaaS

What Success Looks Like

In 30 Days

• Daily standup running; introduced to every stakeholder
• KPI dashboard live; first rep-level performance review delivered to the CRO
• CRM accuracy sweep in place; first data quality audit complete
• Knows every active deal and pilot, its status, and next dependency
• RFP monitoring channels live; first scan delivered to the CRO

In 90 Days

• KPIs tracked daily; reps know their numbers and the team shares one standard for activity discipline
• CRM data visibly cleaner; leadership pipeline reviews are based on numbers the team trusts
• First pilot running under the structured framework with documented criteria and regular check-ins
• Pricing approval queue has a defined SLA and it is being met
• Contract status visible in real time — reps never ask Legal for an update

Why Join Us

• Your work has real stakes. The software you build is what fleet managers open when a concrete truck is late, a hazmat route needs rerouting, or a snow removal crew needs to be redeployed. What you ship matters to the people using it.
• You will own your craft across the full stack, web, mobile, and backend, with the autonomy to make real technical decisions and the influence to shape how the team builds.
• We are growing fast into new verticals and markets, which means the problems keep getting more interesting and the impact of what you build keeps expanding.
• Work remotely from anywhere in Canada, with hybrid options available in Quebec City and Montreal.
• Come together in person at our annual company offsite and stay connected through team activities throughout the year including our running club.