TextExpander has been around for over 20 years, and we’re in a new phase of growth. We’re building more for teams that need consistency, control, and speed in how they communicate.
We're looking for a sales leader who still loves to sell. The team is small right now (one AE), which means this is a true player-coach role: you'll own a number, close your own deals, and help define what "good" looks like across our entire sales motion. That means coaching, building process, and scaling thoughtfully as we add headcount.
This role has a clear path to a full Sales Manager position as the team grows. For now, we need someone who's just as comfortable in a deal as they are developing the people around them.
What You’ll Do
Sell (60% of your time)
Own and close a personal book of business, managing the full sales cycle from prospecting through close
Run discovery calls, product demos, and strategic presentations for mid-market and enterprise prospects
Build pipeline through outbound prospecting, inbound lead follow-up, and strategic account expansion
Consistently hit or exceed individual quota targets while maintaining a healthy, accurate forecast
Develop deep product expertise and become a trusted advisor to prospects on productivity, compliance, and team communication
Lead (40% of your time)
Coach and develop fellow Account Executives through deal reviews, call coaching, and skill development
Run weekly pipeline reviews and help reps identify strategies to advance and close deals
Collaborate with leadership to refine the sales playbook, messaging, and processes that will scale with the team
Partner with Marketing on lead quality, campaign feedback, and content that accelerates the sales cycle
What We’re Looking For
3–5+ years of B2B SaaS closing experience, with a consistent track record of hitting or exceeding quota
Proven experience mentoring, coaching, or informally leading sales peers — you’ve made the people around you better
Experience managing a full sales cycle from prospecting to close with mid-market or Enterprise customers
Comfort selling to a range of stakeholders: from individual champions to VP and C-Suite decision-makers
Strong discovery and consultative selling skills — you lead with curiosity, not a script
Self-starter energy: you manage your time, prioritize ruthlessly, and thrive in a remote, async-first environment
Excellent written and verbal communication skills
A growth mindset: you want the team lead title because you genuinely want to build and develop people, not just manage them
Bonus Points
Experience at an early-stage or growth-stage SaaS company where you wore multiple hats
Familiarity with productivity, workflow automation, or enterprise communication tools
Background in both individual contributor and team leadership roles
Experience with tools like HubSpot CRM, Gong
You’re already a TextExpander power user (seriously, that’s a plus)
Benefits:
High level of autonomy in your role
Motivated and creative teammates
Flexible schedule
Employment benefits:
Healthcare reimbursement plan (ICHRA) — choose your own coverage, reimbursed by us
Paid vacation and sick leave
Company-paid Short- and Long-Term Disability Insurance
Company-paid basic life insurance
Paid Parental Leave Policy
401(k) plan
Salary based on experience
The Fine Print:
TextExpander provides equal employment opportunities (EEO) to all employees and applicants for employment. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.