Senior Enterprise Sales Director jobs in United States
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Lakeside Software · 1 day ago

Senior Enterprise Sales Director

positionAnn Arbor, MI
timeFull-time
remoteHybrid
seniorityDirector/Executive
date8+ years exp

Lakeside Software is seeking a high-performing, strategic outside sales professional to join our Enterprise Sales team in the United States. This role focuses on acquiring new enterprise clients and driving long-term adoption of Lakeside's cloud-based solutions.

AnalyticsBig DataSoftware

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

Qualification

Cloud-based SaaS salesValue-based sellingQuota achievementDigital Employee Experience (DEX)Salesforce (CRM)Pipeline developmentForecastingRelationship buildingCollaboration

Required

Minimum 8 years of experience selling cloud-based SaaS solutions to large enterprise organizations
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

Preferred

Experience in Digital Employee Experience (DEX), digital monitoring, or End User Computing (EUC) highly preferred

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

Company

Lakeside Software

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Lakeside Software helps reduce IT costs and improve end-user experience with systrack digital experience monitoring.
dateFounded in 1997
location
Boston, Massachusetts, USA
people-size201-500 employees
web-link
http://www.lakesidesoftware.com

Funding

Current Stage
Growth Stage
Total Funding
unknown
Key Investors
Insight Partners
2020-02-11Private Equity

Leadership Team

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Mike Schumacher
Founder and CEO
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Brian Curran
Chief Financial Officer
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Recent News

Lakeside Software LLC
Lakeside Software Launches SysTrack AI, Bringing Agentic Digital Employee Experience to Every Device
2025-11-19
Lakeside Software LLC
Lakeside Software Expands Global Footprint with New SysTrack Cloud Region in Azure India
2025-11-06
Lakeside Software LLC
Lakeside Software Named a Leader in ISG’s Provider Lens™ Evaluations for Digital Employee Experience and AI-Enabled Digital Workplace Solutions 2025
2025-10-23
Company data provided by crunchbase