Olly Olly

Account Executive

• Learn and apply the company's sales process and set appointments for senior reps to run and close deals
• Once fully ramped, manage the full sales process from start to finish using a consultative sales approach
• Perform 100% cold-calling to present digital marketing/SaaS solutions tailored to business owners
• Make approximately 70-80 outbound calls per day on average
• Overcome objections and secure new clients as Olly Olly customers (zero account management)
• Participate in daily team meetings and weekly trainings to refine sales skills
• Attend in-office training and adhere to set in-office schedule Monday-Friday

National Account Executive

• Learn and apply company sales process and set appointments for senior reps to close deals
• Once ramped, manage full sales process from start to finish
• Conduct outbound cold calls (70-80 calls per day) to prospective small businesses
• Provide consultative sales conversations tailored to business owners' needs to secure clients
• Overcome objections and qualify leads with a hunter mentality
• Participate in daily team meetings and weekly trainings to refine skills and meet goals

• Learn and apply the company's sales process and set appointments for senior reps to run and close deals
• Once fully ramped, manage the full sales process from start to finish, using a consultative sales approach
• Conduct outbound cold calls (70-80 calls per day on average) to prospect small businesses and secure them as Olly Olly clients
• Present digital marketing and SaaS solutions tailored to business owners' specific needs
• 100% cold-calling role with zero account management responsibilities
• Participate in daily team meetings and weekly trainings to refine skills and exceed goals

People Operations

• Process semi-monthly payroll in Gusto (or similar HRIS/payroll software) and ensure accuracy of employee pay, contractor invoices, bonuses, and deductions.
• Administer benefits enrollment, changes, and terminations (US health benefits, PTO, offshore benefits tracking) and serve as first point of contact for employee payroll and benefits questions.
• Support onboarding and offboarding logistics: set up new hires in HRIS, prepare documentation, coordinate with IT for equipment, process final payroll, benefits termination, and exit records.
• Maintain accurate employee records and HRIS data (personal info, role changes, location updates) and respond to standard employment verification and reference checks.
• Support PTO, leave, and attendance tracking across US and offshore teams; assist with HR communications, templates, and process documentation; maintain confidentiality of sensitive information.
• Serve as a resource for managers on People Ops processes and policy-aligned decisions; guide leaders on documentation for performance conversations; escalate complex matters to People Executive.
• Partner with People Executive on projects (e.g., engagement surveys, policy updates, audits) and support People Ops processes and checklists to ensure consistency and accuracy.

People Operations Generalist

Accounts Receivable

• Manage the subscription lifecycle: plan changes, proration, cancellations, reconciliations, and revenue tracking.
• Own dispute representation: prepare and submit evidence packets to banks/payment processors to protect company revenue.
• Work across modern payment processors (Stripe strongly preferred; experience with Adyen, WorldPay/FIS, Chase Paymentech, Braintree, CyberSource, First Data/Fiserv, PayU, Mollie, etc.).
• Maintain billing workflows in HubSpot, ensuring automation, data accuracy, and cross-team communication.
• Support month-end close: reconciliations, AR aging reports, and revenue reporting.
• Identify and implement process improvements to strengthen dunning workflows, dispute outcomes, and reconciliation accuracy.
• Protect revenue and keep AR processes accurate and scalable in a high-growth environment.

Billing and Accounts Receivable Specialist – B2B Subscriptions

Social Media Manager

• Research target audiences and develop social media campaigns to enhance client reach and engagement.
• Plan, design, schedule, and publish social media posts across Facebook, Instagram, and LinkedIn.
• Independently create high-quality graphics and visuals for posts using Canva (or similar tools).
• Align campaigns with client marketing strategies and collaborate with Account Managers and Coordinators.
• Stay updated with social platform changes and propose new engagement strategies.
• Manage a growing portfolio of ~100–150 client accounts, ensuring copy and creative are consistently on brand.

Social Media Specialist

Full-stack Engineer

• Collaborate with cross-functional teams to design, develop, and deploy web and mobile applications
• Develop, design, and maintain scalable web applications, mobile applications, and backend services
• Write clean, efficient, and well-documented code, ensuring quality and security throughout the development process
• Identify bottlenecks and implement solutions to continually improve software efficiency
• Stay up-to-date with emerging trends and technologies in software development to drive innovation and best practices
• Work in partnership with the VP of Software Engineering to design, test, and implement the product

Staff Software Engineer

Billing Specialist

• Manage the subscription lifecycle in Stripe: new setups, plan changes, proration, cancellations, reconciliations, and revenue tracking
• Own dispute representment: prepare and submit evidence packets to banks/card networks to protect company revenue
• Execute and maintain billing workflows in HubSpot, including automation of tickets and cross-team communication
• Support month-end close: AR aging reports, reconciliations, and cash collection forecasting
• Investigate delinquencies: analyze root cause, adjust accounts, and handle outbound collections calls/emails when needed
• Partner with Sales & Customer Success to ensure accurate subscription data
• Identify and implement process improvements to make AR more efficient and scalable

Senior Billing Specialist, Stripe/Subscriptions

QA Engineer

• Analyze team performance and project data to identify opportunities for improving delivery speed, quality, and efficiency.
• Work closely with the SEO and Digital Marketing Director to enhance workflows, launch new initiatives, and ensure website production supports overall marketing strategy.
• Partner with leadership to spot risks, remove roadblocks, and keep projects on schedule.
• Review and refine the output of the QA, design, and web support teams to ensure error-free, on-brand client websites and digital assets.
• Lead, coach, and develop your team of 10, setting clear expectations, managing workloads, and fostering accountability.
• Collaborate cross-functionally with SEO, digital marketing, and client-facing teams to ensure client deliverables align with business needs and drive measurable results.
• Actively contribute to Olly Olly’s culture by providing regular feedback, sharing best practices, and promoting continuous improvement.
• Identify workflow bottlenecks and standardize processes to ensure smooth project delivery and high-quality client outcomes.

Digital Operations Manager, Web, QA and Design

Operations

• Manage the subscription lifecycle in Stripe: new setups, plan changes, proration, cancellations, reconciliations, and revenue tracking.
• Own dispute representment: prepare and submit evidence packets to banks/card networks to protect company revenue.
• Execute and maintain billing workflows in HubSpot, including automation of tickets and cross-team communication.
• Support month-end close: AR aging reports, reconciliations, and cash collection forecasting.
• Investigate delinquencies: analyze root cause, adjust accounts, and handle outbound collections calls/emails when needed.
• Partner with Sales & Customer Success to ensure accurate subscription data.
• Identify and implement process improvements to make AR more efficient and scalable.

Billing and Accounts Receivable Operations Specialist

• Work with Flutter/Dart to build a multi-platform product that impacts small business owners daily
• Develop, design, and maintain scalable web and mobile applications
• Write clean, efficient, well-documented, maintainable code
• Collaborate with cross-functional teams to design, develop, test, and deploy code
• Troubleshoot and debug production issues
• Contribute across the full software development lifecycle from planning and architectural design to production and deployment
• Support and implement new features to expand the value of the Olly Olly App in the market

National Account Executive

National Account Executive

National Account Executive

People Operations Generalist

Billing and Accounts Receivable Specialist – B2B Subscriptions

Social Media Specialist

Staff Software Engineer

Senior Billing Specialist, Stripe/Subscriptions

Digital Operations Manager, Web, QA and Design

Billing and Accounts Receivable Operations Specialist

Junior Software Engineer