Enterprise Account Executive - Remote

TCP Software; Town of Texas (WI); Remote; USD 70,000 - 100,000; Full time

Benefits offered by this job

Competitive salary

20 Days of PTO

Comprehensive benefits (Health/Dental/Vision/401k)

Job summary

TCP Software in Wisconsin is seeking an Enterprise Account Executive to drive subscription revenue and expand existing accounts. The ideal candidate will have 3–5 years of B2B sales experience and a proven track record of closing deals worth $50K–$250K. Responsibilities include conducting needs assessments, managing the sales pipeline, and effectively communicating product value to customers. TCP Software offers competitive salary, PTO, and comprehensive benefits, making it an excellent workplace for driven sales professionals.

Qualifications

• 3–5 years of B2B sales experience with at least 2 years in full-cycle enterprise sales.
• Proven track record closing deals in the $50K–$250K ACV range.
• Ability to articulate deal strategies and value propositions.

Responsibilities

• Drive recurring subscription revenue via new customers.
• Expand current account revenue through cross-sell/upsell.
• Conduct effective needs assessments across multiple customer groups.

Skills

B2B sales experience

Solution selling

Consultative selling

CRM proficiency

Job description

About TCP

For more than 30 years, TCP has helped organizations engage their people by providing flexible, mobile timekeeping and workforce management solutions. Trusted by tens of thousands of customers and millions of users, TCP delivers best‑in‑class technology and personalized support to organizations of all sizes in the public and private sector to meet their complex timekeeping, employee scheduling, leave management and other workforce needs. Growth is happening and our vision for a successful future is clear – we'd love for you to join us on this journey!

As a Enterprise Account Executive you will:

• Identify as a subject matter expert and advisor to prospective customers, through knowledge of current trends and topics of interest within assigned market segment(s).
• Drive recurring subscription revenue via new customers within a defined territory.
• Expand current account revenue via cross‑sell / upsell from accounts within defined territory.
• Achieve and exceed assigned sales revenue quota by targeting Enterprise account segment.
• Prior experience selling to State & Local Gov’t, K12, and Higher Education a plus.
• Coordinate onboarding of new customers and expansion sales with assigned CSM(s).
• Conduct effective needs assessments across multiple customer groups (technical, business, executive).
• Uncover client key business objectives and challenges, delivering actionable recommendations for improvement.
• Communicate the features and benefits of our niche software products in a consultative manner.
• Perform customized presentations and coordinate product demonstrations with Solutions Consultants.
• Maintain an organized database of accounts, opportunities, and activities.
• Manage, track, and forecast pipeline opportunities with accuracy.
• Develop and maintain ongoing promotion of company capabilities within assigned market segments.

Experience & Track Record

• 3–5 years of B2B sales experience with at least 2 years in full‑cycle enterprise sales.
• Proven track record closing deals in the $50K–$250K ACV range.
• Consistent quota attainment (80%+ over multiple years, ideally 90%+ in the most recent year).
• Experience managing 8–12 active opportunities simultaneously.
• Familiarity working with buyer personas such as IT, Operations, and Finance.
• References that validate both results and relationship‑building capabilities.

Sales Methodology & Skills

• Strong understanding of solution selling and familiarity with MEDDIC or similar frameworks.
• Ability to clearly articulate deal strategies and value propositions with examples.
• Demonstrated consultative selling approach versus transactional/product selling.
• Skilled at discovery questioning that uncovers business problems, not just technical requirements.
• Ability to map product features to business outcomes and quantify ROI.
• Understanding of basic financial concepts (ROI, payback period, TCO).

Deal Management

• Experience running 3–6 months sales cycles with multiple customer touchpoints.
• Ability to navigate basic procurement processes.
• Skilled at coordinating internal resources (SEs, CSMs, executives) effectively.
• Demonstrates pipeline hygiene and forecasting accuracy.
• Consistent CRM use with detailed opportunity notes.
• Familiarity with MSAs, redlines, and basic contract negotiations.

Communication & Presence

• Strong written communication skills for emails, proposals, and presentations.
• Comfortable presenting to director‑level stakeholders.
• Can handle objections professionally and without defensiveness.
• Emotional intelligence and ability to read room dynamics effectively.
• Professional presence that quickly builds credibility.

Industry & Product Fit

• Familiarity with workforce management, SaaS, or adjacent industries.
• Technical aptitude appropriate for complex software solutions.
• Ability to quickly learn and retain product knowledge.
• Previous B2B SaaS or intangible solution sales experience preferred.

Coachability & Culture

• Growth mindset and openness to feedback.
• Curiosity reflected by thoughtful questions about process, product, and customers.
• Strong alignment with TCP values and collaborative mindset.
• Evidence of teamwork over “lone wolf” approaches.
• Realistic and resilient when facing challenges or setbacks.

Physical Requirements

• Prolonged periods sitting at a desk and working on a computer.
• Must be able to lift up to 15 pounds at times.
• Travel up to 25%.

Benefits

• Competitive salary
• 20 Days of PTO and 13 days of company‑wide holidays
• 8 hours to volunteer and impact the community
• Comprehensive benefits (Health/Dental/Vision/401k)
• Employee Choice Pre‑Tax Benefit

TCP is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.