Sales Enablement Analyst

sunday; Chicago (IL); On-site; USD 70,000 - 100,000; Full time

Benefits offered by this job

Stock options

Health insurance (family)

Free vacation policy

Job summary

sunday is hiring a Sales Enablement Analyst to empower its sales teams in the US market. You will coach sellers, run training, and create practical enablement materials to drive faster ramp and stronger selling habits in SMB and mid-market segments.

You'll collaborate with local sales leaders and the global enablement team, own coaching plans, and measure impact to continuously improve training outcomes.

Qualifications

• 2+ years in SMB or mid-market sales, sales enablement, or similar seller-facing role.
• Experience in a high-velocity environment where processes are being built.

Responsibilities

• Support onboarding and ramp for new SDRs and Account Executives in your market.
• Run live training sessions, workshops, mock pitches, and roleplays.
• Conduct call reviews and coaching; translate gaps into coaching plans.
• Build and maintain sales enablement materials (pitch decks, battlecards, FAQs).
• Partner with local leaders to prioritize enablement needs and manage backlogs.

Skills

Sales enablement

Coaching

Analytical thinking

Communication

Training logistics

Project management

Ownership

Tools

CRM systems

Call recording platforms

Job description

About Us

sunday is building the fastest, simplest way to pay in restaurants. With a quick scan of a QR code, diners can pay, tip, and leave in about 10 seconds. We believe great products should feel obvious, not complicated, and we focus relentlessly on keeping things simple while earning trust from restaurants and guests at every interaction. Today, sunday powers payments in thousands of restaurants across the US, UK, and France, helping operators turn tables faster, increase tips, and unlock valuable insights. We push ourselves to go beyond what's expected, building with ownership, moving fast, and scaling with ambition as we tackle our biggest growth opportunity in the US.

About The Role

We are hiring a Sales Enablement Analyst to become the on-the-ground coaching and training arm of our Sales organization. You'll sit within sunday's global Sales Enablement function and work closely with local sales leaders and sellers. Your job is to help sales teams ramp faster, build stronger selling habits, and perform at their best. This is a hands-on individual contributor role: you'll run training, coach sellers, identify performance gaps, create practical enablement materials, and bring product and sales messaging to life in the field. You'll work especially closely with SMB and mid-market sellers serving restaurant operators. You will not be expected to arrive with a perfect playbook. Instead, you'll learn the local sales motion, understand where individual sellers need the most support, and build simple, useful interventions that improve performance.

Join early, grow fast, and shape the journey!

Key Responsibilities

• Support onboarding and ramp for new SDRs and Account Executives in your market, including training logistics, curriculum modules, certification tracking, and ramp reporting.
• Run recurring live training sessions, workshops, mock pitches, roleplays, and objection-handling sessions that help sellers apply what they learn.
• Conduct call reviews, shadowing, and individual coaching; identify specific seller gaps and turn them into practical coaching plans.
• Build, localize, and maintain sales enablement materials such as pitch decks, battlecards, objection handlers, one-pagers, FAQs, talk tracks, and outreach resources.
• Partner with local sales leaders and the global enablement team to prioritize enablement needs and keep a structured backlog of actions.
• Use sales and ramp data, call-quality signals, and feedback from the field to identify trends and recommend targeted support.
• Help sellers understand sunday's products, customer value propositions, restaurant use cases, and evolving sales messaging.
• Support adoption of sales tools, coaching platforms, CRM workflows, sales methodologies, and new product or process launches.
• Share local market insights with the global enablement function so content and training reflect real customer conversations.
• Document what works, measure the impact of enablement activity, and continuously improve the way sellers are trained and supported.

About You

Must-haves

• 2+ years of experience in SMB or mid-market sales, sales enablement, sales training, sales operations, or a similar seller-facing role.
• Experience working in a high-velocity, hands-on environment where processes are still being built and improved.
• Strong communication and facilitation skills: you can explain a concept simply, deliver actionable feedback, and keep a group engaged.
• A practical coaching mindset: you enjoy helping people improve and can adapt your approach to different sellers.
• Analytical rigor: you can use performance data, call observations, and field feedback to identify gaps and prioritize interventions.
• Excellent organization and follow-through across multiple training sessions, content projects, and coaching needs.
• Ownership and bias to action: you are comfortable taking initiative without waiting for a perfect process or complete information.
• Ability to work directly with local operators, owners, GMs, and other SMB/MM stakeholders, or a strong desire to learn this customer environment.

Strong preferences

• Experience in restaurant technology, hospitality technology, payments, POS, ordering, or a related category.
• Experience selling to or supporting sellers serving restaurants, hospitality businesses, or other fast-moving local operators.
• Experience with sales coaching, onboarding, call reviews, mock pitches, roleplays, objection handling, or certification programs.
• Experience working in a Series B-D or similarly fast-scaling company.
• Familiarity with sales tools, call-recording platforms, CRM reporting, and sales methodologies.

What We Offer

• A competitive salary + Stock Options
• Free Vacation Policy
• 100% Employer-Covered Health Insurance for you and your children
• Specific benefits based on location (the job is available in Paris, London or any of sunday's core US metros: Dallas, Miami, New York, Chicago, Atlanta, or Los Angeles.)

sunday is an equal opportunity employer and does not discriminate and all qualified applicants will receive consideration for employment without regard to race, creed, color, sex, affectional or sexual orientation, gender identity or expression, gender, ethnicity, religion, national origin, ancestry, nationality, age, disability, marital status, veteran status, genetic information, or on any other basis prohibited by law (except where an attribute is a bona fide occupational qualification).