Sales Development Representative (PLG / Install-Base Expansion)

About Wispr

Wispr Flow is making it as effortless to interact with your devices as talking to a close friend.

Today, Wispr Flow is the first voice dictation platform people use more than their keyboards — because it understands you perfectly on the first try. It’s context-aware, personalized, and works anywhere you can type, on desktop or phone.

In 2026, in addition to dictation, we're focused on building native actions — an agentic framework that understands you, and works reliably.

We’re a team of AI researchers, designers, growth experts, and engineers rethinking human-computer interaction from the ground up. We value high-agency teammates who communicate openly, obsess over users, and sweat the details. We thrive on spirited debate, truth-seeking, and real-world impact.

We've grown our revenue +150% every quarter for the last 4 quarters, and have raised $81M from Tier 1 VC firms and other well-known angels.

We’re hiring a Sales Development Representative (SDR) focused on expanding Wispr adoption inside existing accounts. This role blends product-led growth, customer engagement, and extremely high-quality written communication to help more teams discover the power of voice.

What You’ll Do

• Analyze product usage patterns to identify champions, emerging power users, and expansion opportunities

• Reach out proactively to existing users to understand workflows and surface adjacent teams who benefit from Wispr

• Drive internal referrals (“Who else on your team would benefit from Wispr?”)

• Create and iterate thoughtful, concise, high-signal messaging across email, in-product, and outreach channels

• A/B test messaging, sequences, and hooks — share what’s working and what’s not

• Map accounts, track adoption trends, and help architect viral loops between users and teams

• Maintain clear, organized pipeline reporting around seat growth, team activations, and internal expansion motion

• Continually refine the PLG playbook — triggers, messaging, activation patterns, and handoff rules

What Makes You a Great Fit

• You write exceptionally well. Clear, direct, user-centric communication is a core part of the job — not an optional skill.

• You’re meticulous about messaging: tone, structure, clarity, and respect for the recipient’s time.

• You’re comfortable iterating quickly, testing hypotheses, and adjusting based on data.

• You enjoy digging into product analytics to understand behavior and identify momentum.

• You thrive in fast-moving environments and enjoy building processes from the ground up.

• Bonus: experience in PLG or tools like Pocus, Endgame, or Catalyst.

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.