Senior Account Executive (MD, DC, or VA - Remote)

Senior Account Executive

Location: Remote Washington, DC metropolitan area (DC, Maryland, Virginia) or Austin, TX (Hybrid, 2 days/week onsite)
Compensation: Competitive base + commission + benefits

About Us

Togetherwork is a $250M recurring revenue SaaS business with over 33 software applications serving 12+ vertical markets. We exist to help communities, organizations, and businesses thrive by delivering software solutions tailored to their unique needs.

With our new headquarters on South Congress in Austin, TX, we are entering an exciting phase of growth. We work hard and play hard. We love our customers, we innovate with purpose, and we won’t stop until we’ve delighted every client across the diverse ecosystem we serve.

About This Role

Togetherwork is seeking a Senior Account Executive to expand our customer base by identifying, engaging, and closing high-value prospects. This role focuses on acquiring multi-location businesses, large national organizations, and Private Equity-backed companies.

You’ll play a key role in driving new logo growth through a proactive, consultative sales approach—leveraging outbound outreach, video meetings, and in-person engagements. This is a high-impact opportunity for a results-oriented sales professional who thrives in building relationships and closing complex deals.

What You’ll Do

• Identify and target new opportunities: Use tools like Google, LinkedIn, Facebook, and industry events to uncover and engage multi-location prospects, franchises, large national groups, and PE-backed organizations.

• Build and manage a strong pipeline: Collaborate with Sales and Marketing to develop a robust funnel of qualified opportunities.

• Lead the full sales cycle: Manage outreach, discovery, solution alignment, product demonstrations, and closing, using a consultative sales approach.

• Conduct professional presentations and demos: Deliver high-impact software demonstrations via Zoom and in-person meetings to C-level and senior decision-makers.

• Develop tailored proposals: Manage RFIs, RFPs, and contract creation, ensuring each proposal reflects customer needs and business goals.

• Collaborate cross-functionally: Work with internal stakeholders to align sales efforts with marketing campaigns, product positioning, and customer success initiatives.

• Own results: Maintain accountability for activity metrics, pipeline generation, and closed revenue, consistently iterating through a test, measure, and learn approach.

What You'll Bring

• 3–5+ years of experience in B2B outbound sales, preferably in SaaS or high-tech environments.

• Proven track record of closing large, complex deals with multiple stakeholders.

• Strong presentation and communication skills—both virtual and in-person—with the ability to tailor messaging to executive audiences.

• Experience managing 3-6 month sales cycles with multiple decision-makers.

• Demonstrated success in generating new business from enterprise or multi-location accounts.

• Excellent negotiation, influencing, and relationship-building skills.

• Entrepreneurial mindset with strong self-motivation, organization, and time management.

• Creative problem-solving and analytical thinking skills to identify customer needs and propose solutions.

• Experience with CRM tools (Salesforce preferred) and other sales enablement platforms.

Why This Role

Impact: Play a critical role in Togetherwork’s growth by securing large, strategic accounts.
Challenge: Tackle long-cycle, multi-stakeholder deals that require strategic thinking and relationship depth.
Ownership: Manage your territory end-to-end with autonomy and accountability.
Collaboration: Partner with Marketing, Product, and Customer Success to deliver cohesive solutions to complex customer challenges.

Compensation & Benefits

Base Salary: Competitive
Commission: Performance-based, uncapped
Benefits:

• Medical, dental, and vision insurance options

• 100% employer-paid short/long-term disability

• Basic Life Insurance

• 401(k) with 100% company match up to 4%

• Flexible paid personal/vacation time built on mutual trust and accountability

• 10 sick days annually

• 10 company-paid holidays

• 6 weeks paid parental leave

Inclusion and Diversity

Togetherwork is an Equal Employment Opportunity Employer. We value diverse backgrounds, experiences, and perspectives. Employment decisions are made without regard to race, color, religion, gender, gender identity, sexual orientation, disability, veteran status, age, national origin, or any other protected category under applicable law.

Interview Process & Expectations
Our interviews are designed to be interactive and conversational. Candidates are expected to respond based on their own experience and thinking during live interviews.

To ensure a fair and consistent interview experience, the use of real-time AI tools or other external assistance to generate or guide interview responses is not permitted. Interviews are intended to reflect an individual’s judgment, problem-solving approach, and communication.