Managing Director - Fluent Software Group (Canada)

A note to prospective candidates: this posting represents a pipeline opportunity. We are a growing organization that believes in getting ahead of our talent needs rather than reacting to them. By building relationships with exceptional leaders today, we position ourselves and you, for success tomorrow. There is no guarantee of an immediate role, but we are genuinely interested in connecting with the right people and keeping the conversation going as our portfolio expands.

About Fluent

Fluent Software Group is part of Valsoft Corporation’s family of operating groups, a global leader in acquiring and growing vertical market software companies. We focus on specialized industries where deep expertise truly makes the difference.

At Fluent, we partner with founders to actively scale what they've built. We bring hands-on operators, proven playbooks, and the resources to accelerate growth, so your business doesn't just continue; it compounds.

The Role

This position provides critical operational leadership to a company and potentially a portfolio of companies within a growing software vertical. As the leader of a Business Unit, you will be responsible for developing and implementing the business’s strategic plan across all major functions, including sales and marketing, R&D, customer service, professional services, and human resources.

You will work closely with the leadership team to identify, define, and execute strategies required to achieve growth plans and operating objectives, with a focus on improving operational excellence. This role carries full accountability for the business unit’s results, making it ideal for a driven leader eager to make a significant impact.

Key Responsibilities

• Own the long-range, annual, and quarterly financial and non-financial goals

• Develop and communicate a clear vision of goals and objectives, strategies, and philosophies about growth, revenue generation, profitability, and customer care

• Manage day-to-day operations, including sales performance, opportunity management, forecasting, R&D capacity, and customer support

• Attend promotional events which include but not limited to tradeshows and panels

Sales and Marketing

• Drive revenue growth, working with the sales team to identify new opportunities and execute growth strategies including cross/upsell and entering adjacent markets

• Develop and implement best in class sales operations and sales infrastructure to enable effective scale and ensure process discipline

• Develop and maintain competitive intelligence programs, generating industry trend reports to inform new feature and product development

• Improve use of Salesforce and other internal tools to increase forecasting capability, implement targets, and provide actionable insights to executive team and board of directors

• Create and implement KPIs for sales team to measure performance and productivity (ex: CAC / LTV); develop performance dashboards and establish reporting process (measure NRR and MRR trends)

• Work with sales leaders in establishing quotas, budgets, compensation plans and pricing optimization

• Manage key relationships with large accounts is mandatory

Customer Care/Customer Success

• Execute an effective, long-term customer success program for clients

• Implement and maintain client support initiatives

• Facilitate both in-house and client training sessions

• Monitor and document Customer Success metrics, including program usage, satisfaction levels, ticket throughput, and resolution

• Coordinate the administration of annual customer satisfaction surveys (NPS) and other communication tools

Research and Development

• Ensure clear product roadmaps are established, followed, and adapted to meet market needs

• Balance investment in R&D with maintenance efforts to maximize new customer growth and retain existing clients while maintaining efficient Customer Care and R&D operations

• Track Product Manager prioritization of R&D tasks, ensuring they are entered into the corporate system and executed by software developers

• Facilitate the growth of Product Managers by aligning their activities with job descriptions

AI Strategy and Agentic Workflow Transformation

As AI reshapes the competitive landscape of software, this role carries direct accountability for ensuring the business unit is not experimenting with AI — but systematically deploying it. The GM is expected to lead the transition from AI-assisted workflows to agentic systems that reduce human intervention, increase throughput, and compound value over time.

• Champion the infusion of AI across all business unit functions — from sales operations and customer success to R&D delivery and financial forecasting — identifying where autonomous systems can permanently replace manual steps

• Define and track the unit’s AI maturity roadmap, measuring progress from assisted tooling to agentic workflows that decide and execute with minimal human oversight

• Partner with R&D leadership to embed AI into the software development lifecycle (SDLC), prioritizing initiatives that move the product from a system of record to a system of action

• Establish clear signal/noise discipline around AI adoption — distinguishing high-impact implementations that compound value from performative experimentation that stalls progress

• Hold teams accountable for documenting AI-driven outcomes: time saved, decisions automated, costs avoided, and quality improvements — translating experiments into measurable business leverage

• Align the team to the future state of agentic AI by building internal capability, sponsoring cross-functional learning (including developer-led spotlights and structured retrospectives), and creating a culture where AI adoption is treated as a core operational competency

• Evaluate and govern AI tool adoption across the unit, ensuring data security, compliance, and vendor accountability are maintained as automation expands

Professional Services

• Ensure we are delivering profitable projects by monitoring billable utilizations, staff OPEX and contribution margin

• Establish strategies to increase NRR

• Track on a monthly basis results with the Head of Professional Services

Financial Management

• Review with Senior Management and the team

• Advance performance by driving improvements in revenue, profit, customer retention, loss prevention, and expense ratios

• Annual, quarterly, and monthly revenue results/forecasts and costs

• Participate in the development of internal department policies and programs to support quality and growth

• Drive P&L, ROI, EBITDA, rule of 40 and ARR/IRR performance of businesses and ensure companies are meeting organizational objectives

Human Resources

Partnering with your HR lead in:

• Driving talent retention and development

• Complying with local employment legislation

• Developing a true local company culture

Growth through M&A

• Engage in M&A activities, working closely with the Valsoft investment group on acquisition strategy and M&A initiatives

• Oversee post-acquisition initiatives to integrate companies into your business unit, focusing on operational transformation and implementation of efficiencies

Knowledge, Skills and Abilities

• Proven experience in senior leadership roles within the software or technology sector

• Strong skills in developing and executing strategic business plans across multiple functions

• Demonstrated success in driving revenue growth and market expansion

• Hands-on approach to managing daily operations and improving operational efficiency

• Demonstrated understanding of AI adoption in enterprise software environments, with the ability to distinguish high-signal AI work from experimentation and drive agentic transformation across business functions

• Comfort operating in ambiguity with the ability to drive clarity, prioritize ruthlessly, and align teams around outcomes rather than activity

Why Fluent?

• High Autonomy, High Impact: Own your work from Day 1

• Serious Career Growth: Exposure to M&A, integration, and scaling operations

• Learning-Driven Culture: We invest heavily in talent development

• Entrepreneurial Energy: No two days look the same

• Competitive Offer: Compensation, Health, dental, vision, PTO, and more

• Team-First Mindset: Regular events, collaboration, and global connections

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