Sales Representative – Legal & Government Sectors

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Speak Write is a tech-driven transcription service that helps legal professionals and protective services agencies eliminate documentation burdens so they can focus on the work that matters. We deliver fast, accurate, and secure transcription — without contracts, long onboarding, or complicated tools.

We’re looking for a self-starting, highly motivated Sales Representative to drive new business from the ground up. You’ll be responsible for generating your own opportunities with law firms and protective services agencies (e.g., child welfare, law enforcement) — engaging prospects, uncovering needs, and presenting how Speak Write can help simplify their work.

This is a high-volume outbound role that requires persistence, creativity, and confidence. You won’t be handed a list of warm leads — you’ll build your pipeline through outreach, insight, and consistency. The good news is that Speak Write has grown this way for the past 25+ years so we can show you the ropes.

• Proactively identify and reach out to potential clients in legal and government sectors.
• Initiate conversations by phone, email, Linked In, or other channels — no scripts, just relaxed, value-driven conversations.
• Build and manage your own sales pipeline.
• Understand prospects’ workflows and challenges, and tailor messaging to show how Speak Write solves them.
• Present demos or overviews of the service (it’s simple and fast).
• Follow up diligently and consistently to close deals.
• Collaborate with the marketing and customer success teams for feedback loops and client handoff.

We’re not looking for a script reader or a churn-and-burn seller. We want someone who is tenacious, smart, and ready to challenge the status quo with an easy-to-use service that saves clients hours every week.

• 2+ years of sales or business development experience (preferably B2B).
• Experience with outbound prospecting and self-sourcing leads.
• A “Challenger” mindset — you educate, tailor, and take control.
• A relaxed, human approach — you connect with people, not personas.
• A strong work ethic and comfort with high activity volume.
• Solid writing and phone communication skills.
• Analytical instincts — you test, refine, and adapt your strategy.
• Familiarity with CRM tools and outreach automation platforms

Experience selling a service to legal professionals or government agencies.

Background in legal tech, SaaS, or professional services.

• A proven product with strong brand recognition in legal and government.
• Flexible, remote work environment.
• Supportive team culture with room to own your role.
• Mission-driven impact — help people reduce burnout and increase productivity.

We’re looking for someone who thrives on initiative and knows how to turn conversations into opportunities. If you’re excited to sell a simple product that makes a real difference — we’d love to hear from you.