Senior Director of Operations, New Products (Conversational)

United States /
Sales /
About Attentive: 
Attentive® is the most comprehensive text message marketing solution, driving 20.5% of total online revenue for businesses by creating thoughtful SMS experiences. Using real-time behavioral data, Attentive makes it possible for businesses to automatically send engaging text messages to each subscriber. Over 4,000 leading businesses like CB2, Pura Vida, Urban Outfitters, Rebecca Minkoff, Steve Madden, and more rely on Attentive and see strong performance, like 30%+ click-through rates and 25x+ ROI.

In March 2021, Attentive announced a Series E investment and is backed by Coatue, Bain Capital Ventures, Sequoia, IVP, and other leading venture firms. 

As our Sr Director, Operations for our Attentive Concierge™ service, you will help build and operationalize a global team of over 1,000 live agents that text in real-time with shoppers. Attentive Concierge provides people-powered text support for brands, making 1:1 personalized and conversational messaging between businesses and consumers possible at scale. 

This leader is creative, driven, analytical and passionate about customer experience, ensuring your live agent team can deliver best-in-class, end to end customer service for our clients. 

You will be reporting directly to our GM, Conversational, and working cross-functionally with sales, client strategy, product, and design to create the operational systems that enable this novel shopping experience.


    • Build and lead a high-performing global team 1000+ live agents (contractors) to consistently meet product demand
    • Source, evaluate, and negotiate contracts for all BPOs and outsourced live agent providers
    • Build our Customer Service operations into a world-class operation and service with scalable and efficient processes and mechanisms that allow us to scale Customer Service as Attentive grows (i.e. closed loop feedback system)
    • Collaborate with the Director of Product Ops to maximize conversation quality and shopper experience as we scale
    • Help shape policy development for the Attentive Concierge team to ensure a safe and positive community for our agents, customers, and end users
    • Track metrics on an individual and team level, work to optimize our people management systems, and report team progress directly to other internal stakeholders on a weekly basis

Skills and Qualifications:

    • 7+ years experience managing operations for large organizations of 100+ outsourced agents and scaling outsourced agent teams by 5-10x
    • 4+ years of strong people management experience
    • Strong record of managing BPO or outsourced live agent provider relationships
    • Excellent analytical abilities, with an ability to think strategically and dive deep to understand inputs, outputs and all associations
    • Exceptional leadership skills; demonstrated ability to effectively communicate, motivate, and inspire cross-functional teams with professionalism and clarity

Benefits & Perks:

    • Robust health benefits packages including access to a 401k and various medical, dental and vision plans, and $100/month fitness reimbursement
    • Full support for remote work
    • Daily lunch delivery credit and other goodies sent to home
    • Regular company-wide social events (even virtually!)
    • Generous annual education stipend toward job-related external learning opportunities
    • An extremely enthusiastic team that appreciates collaboration

    • #LI-remote #LC-1

Attentive is an Equal Opportunity Employer. We’re committed to diversity and maintaining a work environment that is free from harassment and discrimination. We’re committed to them because our core values demand it - values like Integrity First, Listening & Cultivating Discussion, and Default to Action. We believe in embracing “self” and that our true strength lies in the diversity of our employees. For this reason, applicants from all backgrounds are encouraged to apply, and will not be discriminated against on the basis of any protected status under federal, state, or local law.