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Added 2 hours ago
PE
Inside Sales Representative
Peerless Electric
Cornwall, ON
- Full-time
The Inside Sales Representative supports Peerless Electric’s sales activities through independent sales agents and customers. The role handles project inquiries, prepares and follows up on…
Added 3 hours ago
C
Investment Sales Analyst
CBRE
Toronto, ON
- Part-time
CBRE Group, Inc. (NYSE:CBRE), a Fortune 500 and S&P 500 company headquartered in Dallas, is the world’s largest commercial real estate services and investment firm (based on 2024 revenue).…
Added 4 hours ago
GG
Sales Representative
Great Gulf
Orangeville, ON
- Full-time
Gulf Lake Realty is looking for a licensed Sales Representative to join our team at our Orangeville, ON location.
Added 4 hours ago
SM
Service Technician
Swish Maintenance Limited
Winnipeg, MB
- Full-time
As a frontline representative of the company, the Service Technician builds strong customer relationships through professionalism, responsiveness, and technical expertise. Through…
Added 5 hours ago
B
Inside Sales Representative
b62761d3-67ef-479c-8865-4f8052c92bc6
Chilliwack, BC
- $65,000 to $80,000 CAD / year
- Full-time
We are seeking a highly motivated and detail-oriented Inside Sales Representative to support transactional sales activities across our product lines.
Added 5 hours ago
Customer Service Representative - Highway 10 & Raylawson, Brampton (26.25 hrs/week)
Scotiabank
Brampton, ON
Contributing to the Branch’s targets by identifying and fulfilling simple sales opportunities
Added 5 hours ago
W
Technical Sales Representative- Bearings, Power Transmission
Wajax
ON · Stoney Creek, ON
- Full-time
Lead the sales strategy and plan, including customer target accounts, prospecting, sales lead follow-up and maintaining a strong relationship with existing customers
Added 5 hours ago
BG
Trade Marketing Representative - Airdrie, AB
Bentoel Group - A Member of British American Tobacco
Airdrie, AB
- Full-time
Imperial Tobacco Canada - A member of the BRITISH AMERICAN TOBACCO GROUP has an exciting opportunity for a Trade Marketing Representative in Airdrie and the surrounding areas.
Added 6 hours ago
SF
Customer Service Representative
Sunrise Farms
Surrey, BC
- Full-time
…the most current cooking equipment replicating that used in commercial establishments, to facilitate precision testing. This way you know the product you receive will perform to your…
Added 6 hours ago
B
Customer Service Representative
BMO
Surrey, BC
- Part-time
High-level knowledge of personal, commercial and partner offers, and how each can best serve customers’ individual needs.
Added 6 hours ago
Senior Underwriter - Commercial Lines Mid Market-Maritimes
Wawanesa Insurance
Moncton, NB · Dartmouth, NS
Working under minimal supervision, the Senior Underwriter – Commercial Lines, Mid Market is responsible for analyzing the acceptability of complex and high premium volume business according…
Added 6 hours ago
F
Account Manager
Fiserv
Mississauga, ON
- Full-time
Execute add-on sales and upsell/cross-sell initiatives to optimize and protect revenue while controlling renewal compressions.
Added 6 hours ago
A
Field Sales Representative
ALLDATA
Sherbrooke, QC
- $50,000 to $125,000 CAD / year
- Full-time
Central cities to this Sales Representative's territory: Longueeil Rive Sud Montreal & Sherbrook
Added 6 hours ago
A
Field Sales Representative
ALLDATA
Longueuil, QC
- $50,000 to $125,000 USD / year
- Full-time
Central cities to this Sales Representative's territory: Longueeil Rive Sud Montreal & Sherbrook
Added 6 hours ago
W
Inside Sales Representative- Bearings, Power Transmission
Wajax
Timmins, ON
- Full-time
We are seeking a results-driven and customer-focused Inside Sales Representative to join our growing team. In this role, you will act as the primary point of contact for inbound inquiries,…
Added 6 hours ago
Service Technician
Swish Group of Companies
Winnipeg, MB
As a frontline representative of the company, the Service Technician builds strong customer relationships through professionalism, responsiveness, and technical expertise. Through…
Added 6 hours ago
DN
Director, Business Development & Capture
Des Nedhe Group Defence
Ottawa, ON
- Full-time
Confident public speaker and trusted senior-level representative, with excellent executive writing, commercial judgment and discretion.
Added 7 hours ago
A
Migraine, Primary Care Representative - Quebec (13-Month Contract)
AbbVie
Levis, QC
- Full-time
…valued? AbbVie Canada is looking to connect with a Primary Care Representative to join our commercial sales team. This role will cover the South Shore of Quebec, Chaudière-Appalaches and…
Added 7 hours ago
IL
Technical Sales Representative – LED Display & AV Solutions
Inno-Leader LED Technology Ltd.
Vancouver, BC
- $65,000 to $80,000 CAD / year
- Full-time
As we continue expanding our presence in North America, we are looking for a motivated and results-driven Technical Sales Representative to join our team in Richmond, BC.
Added 7 hours ago
3S
Fractional Chief Revenue Officer
3 Step Recruitment Inc.
Waterloo, ON
- Full-time
…seeking an experienced Fractional Chief Revenue Officer / Head of Sales to help build, strengthen and scale its commercial…
Added 7 hours ago
BS
Outside Sales Representative – Building Systems
Bond Securcom Inc.
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Bond Securcom is seeking an experienced Outside Sales Representative to drive business development, generate new commercial opportunities, and build long-term client relationships…
Added 7 hours ago
DI
Business Development Representative
Dig Insights
Toronto, ON · Greater Toronto Area, Canada
- Full-time
…big decisions about their future? The Business Development Representative (BDR) supports Dig Insights' consulting sales efforts by driving early-stage opportunity development across custom…
Added 8 hours ago
J
Residential Leasing Representative
JLL
Toronto, ON
- Full-time
…place where they belong. Whether you’ve got deep experience in commercial real estate, skilled trades or technology, or you’re looking to apply your relevant experience to a new industry,…
Added 8 hours ago
P
Sales and Operations Management Trainee
Penske
Winnipeg, MB
- Full-time
Take charge. Think fast. Move forward. As a Sales and Operations Management Trainee in our fast-paced environment, you will use your hard-earned degree to run a business and quickly solve…
Added 8 hours ago
Manager, Strategy & Distribution - Programs - WSI
Wawanesa Insurance
Toronto, ON · North York - Toronto, ON (Hybr, ON
The Manager, Strategy & Distribution - Programs drives growth of the Commercial Insurance Programs portfolio by developing strategic distribution partnerships. The role leads business…

3 Step Recruitment Inc.

Fractional Chief Revenue Officer

Waterloo, ON, Canada

Compensation: Target annual budget of $100,000-$150,000, depending on experience, scope and employment structure · Full-time

Apply About employer

Applications open in a new tab.

Job details

Pay: Compensation: Target annual budget of $100,000-$150,000, depending on experience, scope and employment structure
Job type: Full-time
Apply by: Nov 25, 2026
Posting language: English
Posted: Oct 26, 2026

Original job description

Fractional Chief Revenue Officer (CRO) / Head of Sales

Location: Kitchener-Waterloo, Ontario

Work Arrangement: Hybrid / Flexible

Employment Structure: Fractional / Part-Time, with potential to become Full-Time

Compensation: Target annual budget of $100,000-$150,000, depending on experience, scope and employment structure

The Opportunity

A growing North American transportation and logistics company is seeking an experienced Fractional Chief Revenue Officer / Head of Sales to help build, strengthen and scale its commercial organization.

Founded in 2019, the company provides freight brokerage and transportation solutions to customers across Canada and the United States. It is now entering an important stage of growth as it prepares to launch a proprietary Transportation Management System (TMS) and client portal that will allow customers to quote, book and track shipments, manage documentation and invoices, and streamline transportation activity through a centralized platform.

The organization is looking for more than a traditional executive advisor. This role requires someone who will work directly with ownership and the sales team to establish structure, improve sales execution, coach representatives, strengthen accountability and help bring a new technology-enabled logistics offering to market.

The successful candidate will combine strategic revenue leadership with hands-on implementation.

Key Responsibilities

Sales Strategy & Process Development

Assess the current sales organization, processes, pipeline and performance
Develop and implement a structured, repeatable sales methodology covering prospecting, discovery, qualification, pipeline management, negotiation, closing and account development
Establish clear sales KPIs, activity expectations and performance standards
Improve CRM adoption, sales reporting, forecasting and pipeline visibility
Develop strategies to win larger and higher-value customers
Identify opportunities to expand revenue within existing accounts
Introduce practical tools, processes and sales disciplines that can scale with the business

Sales Coaching & Leadership

Work directly with sales representatives to improve individual and team performance
Coach representatives on prospecting, discovery, objection handling, negotiation and closing
Participate in sales calls, presentations and demonstrations and provide practical feedback
Establish a consistent sales coaching and performance-development program
Develop sales playbooks, training materials and standardized selling approaches
Help the team transition from selling traditional freight brokerage services to selling broader, technology-enabled logistics solutions
Build a culture of accountability, continuous improvement and measurable performance

Sales Organization & Structure

Evaluate the existing sales organization and recommend improvements to support growth
Help establish clear responsibilities between:
- Account Executives focused on new customer acquisition
- Account Managers focused on retention, relationship management and account growth
Develop processes for customer ownership and account transitions
Review and recommend sales compensation, commission and incentive structures
Establish appropriate performance-management frameworks
Identify future hiring requirements and recommend an appropriate management structure as the sales organization grows

Marketing & Lead Generation

Help establish an effective B2B marketing and lead-generation strategy
Evaluate outbound prospecting, email marketing, LinkedIn, digital marketing, industry events, trade shows and other lead-generation channels
Align marketing initiatives with sales priorities and target accounts
Strengthen market positioning and messaging
Develop measurable marketing objectives and methods for assessing campaign effectiveness
Help differentiate the organization from traditional freight brokerage competitors

Technology & Go-to-Market Strategy

Help develop the commercial launch strategy for the company's proprietary TMS and customer portal
Define market positioning, messaging and value propositions for the technology platform
Work with the sales team to develop effective software demonstrations and presentations
Train sales representatives to communicate the commercial value of the technology
Develop a strategy for converting technology demonstrations into transportation customers
Help position the business as a technology-enabled logistics provider rather than a traditional freight brokerage

Candidate Profile

The ideal candidate is an experienced commercial leader who has successfully built, improved or scaled B2B sales organizations and enjoys working directly with salespeople.

This person should be equally comfortable developing strategy, coaching a representative through a sales call and designing the systems required to support future growth.

Required Experience

Significant senior sales leadership experience as a CRO, VP Sales, Head of Sales or similar commercial leader
Proven success developing and implementing B2B sales processes
Experience building or scaling sales organizations in entrepreneurial or growth-oriented companies
Strong sales coaching and team-development experience
Demonstrated ability to improve individual and team sales performance
Experience designing sales roles, responsibilities and organizational structures
Strong understanding of CRM systems, forecasting, pipeline management and sales reporting
Experience establishing sales KPIs and performance-management frameworks
Experience developing sales compensation and incentive structures
Experience with B2B marketing and lead-generation strategy
Strong negotiation, communication and leadership skills
Ability to balance strategic planning with hands-on execution

Highly Relevant Industry Experience

Experience in one or more of the following would be a significant asset:

Freight brokerage
Third-party logistics (3PL)
Transportation
Supply chain services
Transportation technology
TMS platforms
B2B SaaS
Technology-enabled business services

Ideal Leadership Style

The successful candidate will be:

Hands-on and comfortable working alongside the sales team
Commercially strategic but execution-focused
A strong sales coach
Comfortable challenging existing practices and introducing greater structure
Metrics-driven and accountable
Entrepreneurial and adaptable
Able to communicate effectively with ownership, salespeople and operational teams
Comfortable operating in an evolving growth-stage environment

Why Consider This Opportunity?

Build the Commercial Function

This is an opportunity to help shape the sales organization rather than inherit a fully developed corporate structure.

Direct Access to Ownership

The successful candidate will work closely with company ownership and have meaningful influence over commercial strategy, organizational design and future growth.

Technology Launch

The company is preparing to introduce a proprietary TMS and customer portal, creating an opportunity to help develop the go-to-market strategy for a new technology-enabled logistics offering.

Flexible Structure

The company is primarily considering a fractional / part-time arrangement, but would consider a full-time structure for the right candidate.

Long-Term Potential

As the sales organization and technology platform grow, there may be an opportunity for the scope of the role to expand significantly.

Compensation

The company has established a target annual budget of $100,000-$150,000, with the final structure.

Disclosure:

This posting represents an active and genuine vacancy with one of 3 Step Recruitment’s clients and is not for speculative or pipeline recruitment.

3 Step Recruitment and/or our Clients may use, from time to time, AI-assisted tools to support the screening and evaluation of applications; however, these tools are not intended to replace human judgement or decision-making in the hiring process.

Apply About employer

More about this job

Responsibilities

Build and improve the company’s sales organization by establishing repeatable sales processes, KPIs, CRM and forecasting practices, role structures, compensation frameworks, and coaching programs. Lead marketing and lead-generation alignment and develop the go-to-market strategy for the company’s proprietary TMS and customer portal.

Requirements

Requires significant senior B2B sales leadership experience, a record of building or scaling sales organizations, and strong capabilities in coaching, sales operations, performance management, and marketing strategy. The candidate must balance strategic planning with hands-on execution; experience in freight, logistics, transportation technology, TMS platforms, or B2B SaaS is a significant asset.

Skills

Sales Strategy
Sales Process Development
Sales Coaching
B2B Sales
Pipeline Management
Sales Forecasting
CRM Adoption
Sales Performance Management
Sales Compensation Design
B2B Marketing
Lead Generation
Negotiation
Account Management
Go-to-Market Strategy
TMS Platform Sales
Team Leadership

Visa sponsorship

Not detected in the job text

Keywords

Freight Brokerage
Third-Party Logistics
Transportation
Supply Chain
Customer Portal
B2B Sales
Sales Methodology
Prospecting
Discovery
Qualification
Pipeline Management
CRM
Sales Forecasting
Sales KPIs
Performance Management
Sales Compensation
Account Management
Sales Coaching
Lead Generation
Email Marketing
LinkedIn
Digital Marketing
Trade Shows
Go-to-Market Strategy
Software Demonstrations
B2B SaaS
Negotiation

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