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.
