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
- Prospect and develop new business opportunities within assigned target accounts
- Research and identify key stakeholders, including:
- CIOs
- IT Directors
- Operations Leaders
- Records & Compliance Managers
- Innovation and Transformation teams
- Execute multi-channel outbound campaigns across:
- phone
- LinkedIn Sales Navigator
- webinars
- events
- Identify strategic business triggers such as:
- cloud migrations
- mergers and acquisitions
- compliance initiatives
- reporting challenges
- system integrations
- Conduct consultative discovery conversations to uncover client pain points
- Qualify sales opportunities before transitioning them to senior sales leadership
- Maintain accurate and timely CRM activity documentation
- Support marketing-led campaigns and inbound lead follow-up
- Consistently meet and exceed pipeline generation targets
- Collaborate with leadership, product, and marketing teams to refine go-to-market messaging
Required Qualifications
- 3 years of B2B sales, business development, or lead generation experience
- Experience in SaaS, enterprise software, IT services, or legal-tech preferred
- Strong consultative communication and presentation skills
- Experience engaging mid-to-senior level decision-makers
- Strong account research and personalization skills
- Proficiency with CRM and sales enablement tools, including:
- CRM platforms
- Salesloft
- LinkedIn Sales Navigator
- ZoomInfo
- Strong organization and pipeline discipline
- Ability to communicate technical solutions in business terms
- High resilience and a performance-driven mindset
- Strong desire for career advancement within enterprise sales
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.
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