Sales Development Representative (Enterprise SaaS / Legal-Tech)
At MacroAgility Systems Inc., we deliver enterprise-grade integration, migration, and reporting solutions that help law firms and professional services organizations modernize their operations and gain deeper business visibility.
As we continue to expand across legal and enterprise markets, we are seeking a results-driven Sales Development Representative to play a key role in driving pipeline growth and expanding our market presence.
This is an outstanding opportunity for a high-performing sales professional looking to build a long-term career in enterprise SaaS sales, legal-tech, and strategic business development.
Position Summary
The Sales Development Representative is responsible for generating qualified pipeline opportunities through strategic outbound prospecting and relationship-building.
This role requires a consultative approach to identifying business challenges, understanding client technology environments, and engaging senior decision-makers within target organizations.
You will work closely with sales leadership to drive new business opportunities across law firms, legal departments, and professional services organizations.
This position is ideal for a motivated sales professional who thrives in a fast-paced, growth-oriented environment and is looking to advance into an Account Executive or senior enterprise sales role.
Key Responsibilities
- Prepare sales or other contracts
- Promote Sales to existing clients
- Identify and solicit potential clients
- Assess client's needs and resources to recommend the appropriate goods and services
- Develop reports and proposals to illustrate benefits from use of goods or service
- Deliver sales presentation
- Conduct sales transaction
- Prepare and administer sales contracts
- Conduct transactions through internet-based electronic commerce
- Estimate or quote prices, credit or contract terms, warranties and delivery dates
- Provide input into product design where goods and services must be tailored to suit client's needs
- Consult with clients after sale to provide ongoing support
- Reach out to clients after sale or signed contracts to provide ongoing support
- Review and adapt information regarding product innovations, competitors and market conditions
- Provide clients with presentation on the benefits and uses of goods and services
- Advertise and/or promote products, sales or services
- Provide customer service
- Supervise activities of other technical sales specialists
Supervision
- 3-4 People
Salary:
- 40.06 hourly / 30 hours per week
Specialization- Sales Experience
- Consulting services
- Media Advertising
- Marketing
Additional Information Work Conditions and Physical Capabilities
- Fast- paced environment
- Tight deadliness
Personal Suitability
- Client focus
- Efficient interpersonal skills
- Excellent oral communications
- Organized
- Reliability
- Team Player
- Initiative
- Creativity
- Positive Attitude
Who can apply for this job?
This employer accepts applications from:
- Canadian citizenship and permanent or temporary residents of Canada
- Other candidates, with or without a valid Canadian work permit
By Email
What you must include in your application:
- Cover Letter
- Answer to the following screening questions:
Do you have experience working in this field?
Why Join MacroAgility
- Remote-first, flexible work environment
- Opportunity to sell high-value enterprise SaaS solutions
- Direct exposure to executive leadership
- Clear career progression into senior sales roles
- Growing presence in the legal-tech and professional services market
- Collaborative, high-performance team culture
- Opportunity to work on transformational solutions for global clients
We are an equal opportunity employer and are committed to creating an inclusive environment for all employees. We welcome applications from all qualified individuals regardless of race, religion, gender, sexual orientation, age, disability, or any other protected characteristic. Accommodations are available upon request for candidates participating in all aspects of the recruitment and selection process.
Skills Required
- 1-3 years of experience in sales, business development, or lead generation (B2B preferred)
- Experience or interest in legal-tech, SaaS, IT services, or enterprise software
- Strong written and verbal communication skills
- Confidence speaking with mid-to-senior level stakeholders
- Organized, detail-oriented, and disciplined in CRM usage
What We Do
MacroAgility Systems is a trusted legal tech solutions provider specializing in iManage services for law firms and corporate legal departments. With over 15 years of expertise, we help organizations simplify complex document and email management challenges through tailored implementation, cloud migration, training, and custom development. Our services include: • Cloud & On-Prem iManage Implementation • iManage Upgrades & Migrations (including Work 10, Cloud, and Tracker) • Integration & Custom Development Services • Consultancy & Support for Legal Tech Workflows • iManage User Training & Onboarding We also offer proprietary products that enhance and extend iManage functionality, including: • iSyncKit – Seamless sync for legal documents and workspaces • Export Master & Import Master – Bulk data movement with precision • iReports – Custom legal-centric reporting tools • Workspace Generator – Automated creation of client/matter workspaces • Directory Sync – Real-time integration with Active Directory At MacroAgility, we pride ourselves on hands-on technical expertise, responsive customer support, and a strong track record of solving high-stakes enterprise legal challenges. Our clients span AM Law 100 firms, multinational corporations, and public sector agencies. We don’t just support legal tech. We build it to work better for you.
