Lakeside Software

Monitors IT end-user experience via SysTrack

Senior Enterprise Sales Director

Account ExecutiveConfirmed live in the last 24 hours

Full-timeRemote in USANo salary listedRemote

About the Job

Requirements

At least 8 years of experience selling cloud-based Software as a Service solutions to large enterprise organizations.
Experience in Digital Employee Experience, digital monitoring, or End User Computing is highly preferred.
Proven success selling to enterprise verticals such as Financial Services, Healthcare, and the Public Sector.
Experience partnering with large strategic Channel Partners and Global System Integrators to drive joint success.
Expertise in value-based selling and the ability to articulate financial impact and business outcomes.
A strong track record of quota achievement, pipeline development, and accurate forecasting.
Proficiency in Salesforce and other modern Sales and Marketing engagement tools.

Responsibilities

Drive new business development and expansion strategies within an assigned territory, managing complex enterprise sales cycles from initial engagement to close.
Identify, qualify, and close opportunities with large enterprise organizations while consistently exceeding revenue targets.
Build and maintain multi-threaded relationships across customer organizations, from end users to C-suite executives.
Collaborate closely with the Partner team and Global System Integrators to maximize deal value and strategic alignment.
Deliver tailored, value-based solutions aligned with customer needs and demonstrate clear return on investment and business impact.
Maintain accurate revenue forecasts and manage pipeline, accounts, and time effectively.
Contribute to team success through strategic collaboration and shared goals.

Desired Qualifications

Experience in Digital Employee Experience, digital monitoring, or End User Computing.

Senior Enterprise Sales Director

Lakeside Software · United States (Remote) · Full-time · Posted 2025-09-26

Workplace: remote

Department: Sales

Description

Lakeside Software is seeking a high-performing, strategic outside sales professional to join our Enterprise Sales team in the United States. This individual contributor role (Global Accounts Director) is focused on acquiring new enterprise clients and driving long-term adoption and retention of Lakeside’s cloud-based solutions. It is not a post-sale Account Executive, Management role or Customer Success role; instead, it requires a hunter mindset and a proven ability to build and expand relationships across enterprise organizations with growth opportunities.

Key Responsibilities:

Drive new business development and expansion strategies within assigned territory, managing complex enterprise sales cycles from initial engagement to close.
Identify, qualify, and close opportunities with large enterprise organizations, consistently exceeding revenue targets.
Build and maintain multi-threaded relationships across customer organizations, from end users to C-suite executives.
Collaborate closely with Lakeside’s Partner team and Global System Integrators (GSIs) to maximize deal value and strategic alignment.
Deliver tailored, value-based solutions that align with customer needs and demonstrate clear ROI and business impact.
Maintain accurate revenue forecasts and manage pipeline, accounts, and time effectively.
Contribute to team success through strategic collaboration and shared goals.

Requirements

Minimum 8 years of experience selling cloud-based SaaS solutions to large enterprise organizations.
Experience in Digital Employee Experience (DEX), digital monitoring, or End User Computing (EUC) highly preferred.
Proven success in selling to enterprise verticals such as Financial Services, Healthcare, and the Public Sector.
Demonstrated experience partnering with large, strategic Channel Partners and GSIs to drive joint success.
Expertise in value-based selling, with the ability to articulate financial impact and business outcomes.
Strong track record of quota achievement, pipeline development, and accurate forecasting.
Exceptional collaboration and relationship-building, with strong personal accountability, across internal and external stakeholders at all levels.
Proficient in Salesforce (CRM) and other modern Sales and Marketing engagement tools.

Benefits

Medical, Dental & Vision Insurance
Flexible Spending
Short & Long Term Disability Insurance
Company Paid Life & Voluntary Life & AD&D Insurance
401(k) matching
11 Days Observed Holidays
20 Days PTO
5 Days Paid Sick Time
Opportunities for career development and growth
A collaborative and supportive team culture

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Apply at Lakeside Software

About the Company

Lakeside Software

Monitors IT end-user experience via SysTrack

Lakeside Software provides Digital Experience Monitoring for large enterprises, focusing on improving IT performance and end-user productivity with its flagship SysTrack. SysTrack collects data from endpoints like computers and servers to measure performance and user experience from the user’s perspective, helping IT teams identify issues, optimize resource use, and boost productivity. The product is offered primarily through subscription licenses, and Lakeside also provides consulting services to help organizations implement SysTrack effectively. What sets Lakeside apart is its emphasis on end-user experience and workspace analytics for enterprise environments, combined with ongoing licensing and advisory services to drive IT cost reductions and better performance. The company’s goal is to help organizations reduce IT costs, improve system performance, and enhance user satisfaction by delivering actionable visibility into IT operations.

Company size: 51-200
Company stage: Growth Equity (Venture Capital)
Total funding: Not listed
Headquarters: Boston, MA
Founded: 1997

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