Vice President, Outside Sales

Vice President Of Outside Sales

Net at Work is seeking a proven, high-impact Vice President of Outside Sales to lead and evolve our field sales organization. This role owns the performance, scalability, and execution rigor of our new business sales engine across multiple practices.

Today, this leader will inherit an organization of approximately fifty (50) team members, including:

• Managers of Account Executives
• A centralized Sales Engineering team
• Frontline sellers across multiple practices

We are at an inflection point as a company. The business is performing, and we have aggressive growth goals. This role is both about:

• Scaling what is working, and
• Fixing what is not yet operating at the level we need

This is a builder, operator, and player-coach role. You will not just "run the number" — you will personally help design, inspect, and enforce the systems, operating cadence, and leadership behaviors that make hitting the number predictable and repeatable.

This leader is expected to be deeply involved in the day-to-day realities of selling, including pipeline inspection, deal coaching, forecasting reviews, and frontline leadership. This is not an arms-length or advisory VP role.

This role is a core member of the sales and executive leadership team and will work closely with Marketing, Practice Leadership, BDR, and Delivery.

Job Responsibilities

What You Will Own

• Full ownership of new business bookings performance across the field sales organization.
• Leadership and development of a multi-layer sales organization (approximately 50 people today).
• Hands-on ownership of the revenue operating cadence, including forecasting, pipeline reviews, inspection, and execution discipline.
• The structure, roles, capacity models, and coverage strategy of the sales team.
• Sales leadership team performance and effectiveness.
• Sales Engineering alignment, productivity, and impact.
• The full revenue system from lead → close → delivery handoff, including accountability for breakdowns and leakage.
• Cross-functional alignment with Marketing, BDR, and Practice Leadership.
• Publisher and partner relationships and co-selling motions.
• Compensation plans, incentives, and performance management systems that reinforce desired selling behaviors and recurring revenue growth.

What You Will Do

• Lead the organization to materially increase new logo production, average deal size, and win rates
• Build a predictable, high-integrity forecasting and pipeline management discipline
• Personally inspect deals, pipelines, and forecasts, and coach leaders and sellers in real time
• Standardize and enforce a scalable, inspectable sales process across practices
• Upgrade talent where needed and continuously raise the bar on performance
• Improve funnel conversion, sales productivity, and time-to-ramp for new hires
• Actively participate in key deals, negotiations, and strategic opportunities
• Partner with Marketing and BDR leadership to improve conversion quality and ROI
• Create a high-performance, high-accountability sales culture
• Ensure clean handoff to delivery and long-term client success
• Travel approximately 30%

What Success Looks Like

In the first 12–18 months, you will have:

• Built a high-confidence, accurately inspectable forecasting and execution cadence
• Delivered significant, sustained growth in new business bookings
• Improved conversion rates across the funnel
• Increased sales productivity per rep and per manager
• Strengthened a coaching-driven leadership bench with strong operating discipline
• Created a scalable revenue operating system that supports continued growth

Job Requirements

• 12–20 years of experience in complex B2B technology and/or services sales
• Demonstrated experience leading while remaining close to frontline selling and deal execution
• Proven success scaling and professionalizing a sales organization, not just maintaining one
• Deep experience in:
• Forecasting and pipeline governance
• CRM-driven execution and inspection rigor
• Sales process design, enforcement, and continuous improvement
• Sales capacity and coverage modeling
• Strong track record of building, coaching, and upgrading sales leaders
• Experience in mid-market solution or services sales environments (ERP, SaaS, or similar preferred)
• Comfort owning modern sales systems and tooling decisions (CRM, enablement, analytics, AI-assisted workflows), even if execution is delegated
• Highly analytical, operationally rigorous, and execution focused
• Strong executive presence and cross-functional leadership skills

Leadership Traits We Value

• High standards and low tolerance for mediocrity
• Data-driven, structured, and rigorous operator
• Equally comfortable in strategic discussions and deep execution reviews
• Strong talent evaluator and developer
• Bias for action and accountability
• Customer-centric and reputation-driven
• Thrives in scale, change, and complexity

Why This Role Is Compelling

• Real scope and real impact
• A team, a platform, and investment already in place
• Clear executive commitment to aggressive growth
• The opportunity to build a best-in-class mid-market sales engine, not just manage one.

Customer Requirements

This job may require access to customer information, systems, and/or premises. As a result, this job may require customer approval for such access as an essential job function.

Core Competencies

• Client Champion – Relentlessly exceed client expectations. Consistently anticipate needs to deliver valuable solutions and extraordinary outcomes.
• Problem Solver – Smart, analytical, inquisitive, knowledge-seeker that thrives on a challenge.
• Promise Keeper – Place high value on keeping our word and doing the right thing. Demonstrate honesty, integrity, and commitment.
• Collaborative Integrator –Team player, unifier, relationship-oriented, win-win seeker, exemplify the concept of relationships through trust and unity.
• Driven Intrapreneur – Exceed goals using independent creative thinking, optimism, self-confidence, and a can-do attitude.
• Inspiring Coach – Help employees, clients and partners using knowledge, expertise, experience, and situational fluency.

Compensation and Benefits

Base salary range: $170,000 to $250,000.

This position is also eligible for commissions in accordance with the terms of the Company's plan.

Please note that the quoted pay range for this job is a general guideline only and not a guarantee of compensation or salary. Additional factors considered in extending an offer include (but are not limited to) experience, including industry or product-specific experience, education, knowledge, skills, and abilities, as well as internal equity, alignment with market data, and/or other applicable laws.

We provide competitive, affordable, and diverse benefit programs that support your total health – from healthy body to healthy mind. These benefits support you and your family in all aspects of life:

• Health and Welfare (Medical, Dental, Vision)
• Accident, Critical Illness, and Hospital Indemnity
• Employee Assistance Program (EAP)
• Life and AD&D Insurance
• Short- and Long-Term Disability Insurance
• Flexible Spending Accounts
• Transportation and Parking Accounts
• Health Savings Accounts (with company contribution)
• Retirement Planning (401k with matching contribution)
• Legal Benefits
• Identity Theft Protection
• Pet Insurance
• Wellness Program Offerings
• Paid Time Off, accrued per pay period based on years of service starting at 15 days annually.
• 8 Paid Holidays per year, including 1 floating holiday.

The compensation