Technology Specialist Jobs in Illinois

Alpha | Winfield, IL / Chicago Area

Full-time

Base salary: $75,000-$85,000 + performance bonus eligibility

Travel: Approximately 50-75% in the field

ABOUT ALPHA

Alpha helps small and medium-sized restaurants succeed through POS systems, payments, restaurant technology, and dependable support.

We take a consulting approach. We learn how each restaurant operates, understand what the owner is trying to accomplish, and help them use technology in ways that actually improve the business.

Our mission is simple: Turn tech into profit.

We are an entrepreneurial, growth-stage company that believes restaurants should not have to choose between good technology and people who genuinely care about their success.

THE OPPORTUNITY

This is a relationship-driven customer success role for someone who understands restaurants and likes solving real business problems.

You will own the ongoing relationship with a portfolio of approximately 200 restaurant clients and growing across the Chicago area.

Your job is not simply to check in with customers. You will become someone restaurant owners trust to understand their operation, help them get more value from their technology, identify opportunities for improvement, and take ownership when something goes wrong.

The role combines customer relationships, restaurant consulting, technology, retention, and account growth.

You will report to the Sales and Growth Manager and work closely with Alpha's Support, Projects, Sales, Finance, and technology partners.

WHAT YOU WILL OWN

Build trusted restaurant relationships. Develop strong relationships with owners, operators, and managers. Learn how each business operates, what matters to the owner, where they are struggling, and where Alpha can create more value.

Help restaurants improve. Identify practical opportunities to increase sales, save time, reduce errors or costs, improve online ordering, strengthen loyalty, improve reporting, simplify staff workflows, and make better use of restaurant technology.

Conduct meaningful customer consultations. Review sales trends, technology usage, service history, digital ordering, previous commitments, and opportunities before customer meetings. A successful conversation should create value, useful information, a decision, or a clear next step.

Own customer recovery. When a client becomes frustrated or loses confidence in Alpha, take the lead on the relationship. Understand the problem, coordinate a recovery plan, communicate proactively, and remain involved until the customer is confident in the outcome.

Drive technology adoption. Learn Alpha's supported POS systems, payments, handhelds, online ordering, loyalty, marketing, gift cards, reporting, kitchen workflows, hardware, integrations, and other restaurant technology.

Grow existing accounts. Recommend appropriate upgrades and complementary solutions when they can genuinely improve the restaurant's operation.

Keep promises moving. Restaurant owners should not have to chase Alpha. Maintain clear next steps, owners, deadlines, and customer updates. When another team performs the work, stay involved until the customer outcome is verified.

WHAT SUCCESS LOOKS LIKE

Customers trust you and Alpha, see measurable value from their restaurant technology, and choose to stay and grow with us.

Performance is evaluated through:

Customer retention

Meaningful relationship coverage

Technology adoption

Documented business results

Recovery of at-risk customers

Profitable account growth

Customer commitments completed as promised

WHO WE ARE LOOKING FOR

Restaurant experience is particularly valuable.

Strong backgrounds may include:

Restaurant General Manager or Assistant General Manager

Multi-unit restaurant operations

Customer Success

Account Management

POS or payments

Restaurant technology training

Restaurant consulting

You do not need to arrive knowing every technology platform Alpha supports. We care more about whether you can earn an owner's trust, understand restaurant operations, learn technology quickly, solve problems, and follow through.

You should be comfortable:

Visiting restaurant customers regularly

Building long-term relationships with owners

Handling difficult customer conversations calmly

Managing many simultaneous commitments

Learning technical products

Investigating answers you do not already know

Understanding basic restaurant and business metrics

Recommending solutions without overselling

Working independently in the field

Using modern AI tools while verifying their output

WHO WILL DO WELL HERE

You genuinely like restaurants and restaurant owners.

You are curious about why a business performs the way it does.

When something falls between departments, your instinct is not to say, "That's not mine." Your instinct is to identify the right owner, keep the commitment visible, and make sure the customer gets the result.

You like the idea of returning to a restaurant months after making a recommendation and being able to show the owner that something actually improved.

COMPENSATION AND BENEFITS

Base salary: $75,000-$85,000 annually, depending on experience and qualifications.

The role is also eligible for annual performance bonuses based on established personal, Growth-team, and company performance targets.

Full-time benefits include:

Health insurance

Dental insurance

Vision insurance

Life insurance

SIMPLE IRA retirement plan

Paid time off

Applicable holidays and sick leave

Mileage and approved travel reimbursement

Gym reimbursement

Book of the Month or Audible benefit

Training and professional development

WORKING ARRANGEMENTS

Standard hours are Monday-Friday, 8:30 a.m.-5:00 p.m. Central Time.

When you are not scheduled to meet with customers, you will work from Alpha's Winfield, Illinois office.

Approximately 50-75% of the role is spent traveling, primarily meeting restaurant customers throughout the Chicago area.

Approved mileage and business travel expenses are reimbursed. Occasional overnight travel may be required but is not expected to be routine.

Because restaurants operate beyond traditional office hours, significant customer situations occasionally occur outside standard business hours. Growth Specialists are expected to respond promptly to urgent relationship escalations, with backup coverage available when they are unavailable.

Pay: $75,000.00 - $85,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Retirement plan
• Vision insurance

Work Location: Hybrid remote in Winfield, IL 60190