Role Purpose:

The Sr. Manager of Sales Tooling & AI is a strategic and technical leader responsible for architecting, optimizing, and scaling Groupon’s sales technology ecosystem, with primary ownership of Salesforce and Salesloft. This role sits at the intersection of Sales, Sales Operations, Engineering, and Analytics, ensuring our sellers are equipped with intuitive, automated, and AI-enabled tools that drive productivity and performance.

This leader will modernize and simplify a historically layered sales tech stack by establishing a clear point of view on systems architecture, automation strategy, and AI-forward solutioning. The mandate is not simply to administer tools, but to transform them into a competitive advantage by reducing friction, improving data integrity, and enabling intelligent workflows that drive measurable commercial outcomes.

The Sr. Manager will lead a high-performing team of Salesforce Administrators and Business Program Managers responsible for CRM governance, sales engagement optimization, automation, integrations, and continuous innovation across the sales technology landscape.

Key Responsibilities:

Sales Technology Strategy & Architecture

• Define and own the strategic roadmap for Salesforce, Salesloft, and the broader sales tech ecosystem.
• Establish scalable architecture standards, governance models, and integration frameworks.
• Partner with Sales Leadership and Sales Ops to translate business priorities into system capabilities and workflow design.
• Rationalize legacy tools and technical debt to simplify the seller experience.

Salesforce Ownership & Optimization

• Serve as the executive owner of Salesforce strategy, configuration, data model integrity, and user experience in conjunction with the Engineering department.
• Lead enhancements across pipeline management, forecasting, account hierarchy, territory alignment, and reporting.
• Drive automation of manual workflows and process improvements.
• Ensure data governance standards and scalable object architecture that supports evolving business models.

Salesloft & Sales Engagement Excellence

• Own the strategy, implementation, and optimization of Salesloft.
• Design structured cadence frameworks aligned to funnel strategy and segmentation.
• Improve seller adoption through workflow integration with Salesforce and enablement best practices.
• Leverage Salesloft analytics to continuously refine outreach effectiveness and pipeline generation.

Automation & AI Forward Solutioning

• Identify and implement automation opportunities that eliminate low-value administrative work for sellers.
• Partner with Data & Analytics to embed AI-driven insights into daily sales workflows (e.g., next-best-action, prioritization, lead scoring).
• Evaluate and pilot emerging AI tools that improve seller productivity, forecasting accuracy, and engagement quality.
• Ensure AI initiatives are practical, measurable, and integrated into core operating processes.

Reporting, Insights & Performance Enablement

• Collaborate with Analytics to define the core sales data model and system-driven metrics.
• Enable real-time visibility into pipeline health, activity effectiveness, and productivity drivers.
• Ensure tools reinforce desired sales behaviors and align with incentive design and performance frameworks.

Change Management & Adoption

• Lead change management for new tools, automations, and system enhancements.
• Drive high adoption through structured communication, training, and feedback loops.
• Establish clear SLAs, intake processes, and prioritization frameworks for system requests.

Team Leadership & Cross-Functional Partnership

• Build and develop a high-performing Sales Tooling team, including Salesforce administrators, system analysts, and automation specialists.
• Act as a trusted partner to Sales Leadership, Marketing, Engineering, Finance, and Data teams.
• Balance speed and innovation with governance, compliance, and long-term scalability.

Qualifications:

• 8–12+ years of experience in Sales Operations, Revenue Operations, Sales Technology, Engineering, or related roles in mid-to-large enterprise environments.
• 5+ years of deep, hands-on Salesforce experience, including architecture, automation (Flows), integrations, and data governance. Salesforce Admin and/or Advanced Admin certification strongly preferred.
• Strong expertise in Salesloft (or comparable sales engagement platform) with demonstrated success driving adoption and measurable productivity gains.
• Proven experience designing and implementing automation strategies that improve sales efficiency.
• Exposure to AI-enabled sales tools, predictive modeling, or workflow intelligence solutions.
• Experience leading and developing technical or systems-focused teams.
• Strong stakeholder management skills in matrixed, cross-functional environments.
• Highly analytical, systems-oriented thinker with the ability to connect tooling decisions to commercial outcomes.

We Are Looking For:

• Systems Architect: Thinks in terms of scalable design, clean data models, and long-term sustainability.
• Product Mindset Operator: Treats Salesforce and Salesloft as evolving products, not static tools.
• Automation Champion: Obsessed with eliminating manual effort and increasing seller focus on revenue-generating activity.
• AI Pragmatist: Excited about AI innovation but disciplined in applying it where it drives measurable impact.
• Adoption Driver: Understands that a tool only matters if sellers use it effectively and consistently.

How We Measure Your Success:

First 2-3 Months

• Clear, documented sales tooling roadmap aligned to commercial priorities.
• Improved Salesforce data hygiene and workflow efficiency.
• Increased Salesloft adoption and measurable improvements in activity-to-pipeline conversion.
• Reduction in manual seller administrative time through automation initiatives.

3–6 Months

• Embedded AI-driven workflows that improve prioritization, forecasting accuracy, and outreach effectiveness.
• Streamlined tech stack with reduced redundancy and improved integration stability.
• Measurable gains in seller productivity and pipeline velocity attributable to tooling enhancements.

Longer Term

• A sales technology ecosystem that is intuitive, scalable, and AI-enabled.
• Sellers spending more time selling and less time navigating systems.
• Sales Tooling recognized as a strategic lever for revenue growth and operational excellence.

Why You'll Love Working Here:

• High-impact role with visibility to senior leadership – Help shape the systems that power Groupon’s global sales organization.
• Opportunity to influence the future of a global public company – Play a key role in modernizing the technology and workflows that drive our commercial growth.
• Entrepreneurial environment where your contributions matter – Move quickly, simplify complexity, and see your work translate into real business impact.
• A culture that values curiosity, ownership, and results – We empower people who take initiative, challenge the status quo, and deliver outcomes.

The Details:

• Location: Downtown Chicago (hybrid, 3 days a week in-office)
  • Alternate location: Open to candidates living in València, Spain
• Salary Range for Chicago: $120,000 – $150,000, plus eligibility to participate in a performance-based bonus program.
  • Estimated Total OTE: $150,000 – $187,500+
• Benefits: Medical, dental, vision, EAP, 401(k) match, ESPP, life and disability insurance, FSAs, flexible PTO, and more.

Who We Are:   

At Copperstate Farms and Sol Flower, we’re creating a better kind of cannabis company. Where we know happy plants begin with happy people. We aspire to high standards, take pride in our work, and drive for better results every day. At the greenhouse, our roots are growing flower, but we’ve branched out to offer an extensive range of cannabis products like edibles, topicals, and concentrates for retail dispensary locations. From farm to market, we are committed to the quality of our products and are always testing for patient and customer safety. By bringing together best practices from big agriculture, consumer packaged goods, and pharmaceutical and retail industries, Copperstate is becoming one of the top cannabis companies to work for.    

What We’re Growing:   

As one of the largest greenhouse cannabis producers in North America, Copperstate Farms ranges over 1.7 million square feet of canopy and 40 acres under glass. It’s here where we have been growing a house of cannabis brands that our patients and customers can trust, each addressing a different needs state and demographic. From the greenhouse to corporate to multiple Sol Flower dispensaries, we’re an inclusive cannabis community empowering wellness for all. Most of all, we strive for a culture where our employees view us as one of the best places to work.     

Job Description: 

The Shift Lead is responsible for providing an outstanding customer experience while working closely and collaboratively with other retail staff members to meet revenue goals, lead the retail team, and develop the dispensary staff. The Shift Lead should have a genuine passion for the Cannabis industry and the well-being of its customers and staff. The Shift Lead will ensure that customers’ needs and expectations are met through optimal product selection and top-notch customer service. Ideal candidates should be strong people developers, possess excellent communication and problem-solving abilities, be action-oriented and committed to the highest level of service. 

Core Responsibilities: 

Duties of this job include, but are not limited to: 

• Drive the shift and motivate an elevated level of service and productivity amongst the dispensary team; assist in operations such as opening and closing procedures.
• High level proficiency and ability to perform the position of Store Associate throughout the shift.
• Ability to hit sales KPI’s at the highest level as well as teach and coach Store Associates to elevate individual and store performance.
• Maintain a clean and organized work environment.
• Answer questions or assist with escalated customer issues to ensure efficient flow and operation of the front of the house.
• Work effectively and respectfully with fellow co-workers and other team members.
• Expert level proficiency in all aspects of retail dispensary duties.
• Communicate and recognize employees to promote a positive team culture.
• Assist in training new employees on policies, processes, procedures, and roles.
• Handle customer and employee requests appropriately.
• Provide administrative and managerial support to General Manager and Assistant General Manager.
• Proficiency in all aspects of cash handling including but not limited to cash drops, closing registers and cash audits.
• Balance cash registers and ensure accurate daily deposits.
• Adhere to all cannabis state-specific regulations and laws to execute and enforce compliance efforts.
• Participate in ongoing education and professional development opportunities.
• Manage operations for smooth opening and closing procedures per hours of operation.
• All administrative duties relating to the POS system which can include but are not limited to: Inputting purchase orders, running product reports, and identifying trends.
• Additional duties as assigned by management.

Commitment & Dependability: 

• Willingness to be an integral member of a successful team.
• Dedication to provide the highest levels of service.
• Excellent attendance and reliability.
• Adherence to company policies and procedures.
• Expectation to work evenings, weekends and holidays as required.
• Properly handle confidential customer information and other non-public company proprietary information.

Qualifications and Education: 

• Must be at least 21 years of age.
• Must be able to pass a background check in order to obtain, and maintain, a Facility Agent card in accordance with Arizona State Department of Health Services requirements.
• Minimum of 1 year supervising or retail management experience with at least 1-2 years dispensary experience.
• Associates or bachelor's degree is preferred; or equivalent combination of education and experience.
• Technologically advanced individual with working knowledge of cannabis POS (point of sale) systems.
• Outstanding leadership, organizational, interpersonal, time management and communication skills.
• Strong attention to detail.
• Knowledge of the cannabis industry.

Physical Requirements: 

• Requires prolonged sitting, standing, walking, bending, lifting, and use of hands.
• Frequently required physical exertion to manually move, lift, carry, pull, or push heavy objects or materials.
• Frequently stooping, bending, and reaching.
• Must work indoors and outdoors year-round.
• Must work in noisy and crowded environments.
• Lift 25-50 pounds from the floor to a waist-high table when necessary.
• Crouch & bend often.
• Stand for short/high periods of time.
• Sit for short/medium periods of time.
• Walk for short/high periods of time.
• Occasionally sit on the floor or at floor level.
• Handle the responsibilities and routine stress often associated with this position.

Certifications or Training Requirements: 

• New Hire Orientation & Security Training – New Hire.
• Store Associate Training- New Hire.
• Cannabis Education course – New Hire.
• Additional annual or ongoing training as assigned by management.
• Maintain active Arizona Facility Agent Card – Biannual or as dictated by Arizona Department of Health Services.

Disclaimer: This is not necessarily an exhaustive list of all responsibilities, duties, skills, efforts, requirements or working conditions associated with the job. While this is intended to be an accurate reflection of the current job, management reserves the right to revise the job description or require that other or additional tasks be performed as assigned.