System Operations Lead

United States /
Client Strategy /
About Attentive: 
Attentive® is the leader in conversational commerce, reinventing business to consumer communication. Our SMS-first software platform helps everyone from entrepreneurs to enterprises strengthen relationships with their consumers in a new way. Through two-way, real-time, personalized communications, we drive billions in e-commerce revenue and over 5,000 leading brands like CB2, Pura Vida, Urban Outfitters, Jack in the Box, and Coach rely on Attentive to deliver powerful commerce experiences.

The System Ops team is tasked with optimizing tools to solve business problems, and ultimately move us toward a higher tech touch model with greater efficiencies for our most valuable resource (our people). This team touches every aspect of the customer lifecycle and fundamentally works to stand up net new processes and workflows in service of rapid growth and serviceability.

We are looking for an autonomous self-starter who can both lead by holding others accountable, and own by holding themselves accountable, in order to proactively identify areas of improvement for our 500-person Customer Success organization.


    • Own the operationalization & architecture of specific tools leveraged by the Customer Success organization
    • Work cross-functionally to improve Salesforce workflows, troubleshoot data gaps, and “failproof” our data capture mechanisms
    • Proactively ideate ways of elevating the work of our Client Strategy Managers to eliminate repetitive tasks and manual error prone processes
    • Stand up systems-related initiatives to solve core business problems; accordingly be able to expertly train, “explain” (update resources), and roll out these initiatives
    • Determine how functional teams across Customer Success are spending their time, and isolate means of leveraging existing and/or ideal systems to reduce time spent on tasks that detract from more nuanced and impactful client management

Skills & Qualifications

    • 3+ years experience in operations at a SaaS startup or high growth technology company
    • Experience supporting GTM teams preferred
    • Articulate and organized in thought and speech
    • Ability to execute and recover expeditiously
    • Experience working with CRMs and data visualization tools (like Looker)
    • Experience scaling teams 2-3x annually a plus
    • General interest in the B2B vendor landscape

Benefits & Perks

    • Medical, Dental, Vision Insurance (2 of our plans are $0 premium cost to employees!)
    • Life Insurance - Attentive pays for life insurance equal to 1x your salary (through Anthem)
    • Daily lunch delivery stipend
    • Yearly professional development stipend 
    • One time fitness equipment stipend
    • Monthly fitness stipend 
    • 100% remote work as well as WeWork memberships for those who prefer an office
    • Up to 18 weeks New Parent Leave with 100% pay

    • #LI-remote #LI-as1

Attentive Company Values
Default to Action - Speed is our best offense and defense
Never Settle - Continuously raise the bar for yourself and your teammates
Hard Work Solves Big Problems - Success requires grit and resilience
Be Attentive - Work together as a team to drive greatness for our company and our customers 

If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.

At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation.