About the role
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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About Lakeside Software
Lakeside Software is a leader in cloud-based digital experience management. Lakeside's Digital Experience Cloud, powered by SYSTRACK, gathers and analyzes data on everything that may impact end-user experience and business productivity and provides the unmatched visibility IT teams need to design and support rapidly changing digital workplaces. Customers use Lakeside's technology to perform end-user experience management, digital workplace planning, IT asset optimization, remote work management, and proactive service desk operations.
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Job details
Location
Chicago, IL
Funding
Last stage
Growth
Investors
Founders
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.