Senior Conversation Designer, Seller Experience

  • Full-time

Company Description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

To solve this problem, we expanded into software and built integrated solutions to help sellers sell online, manage inventory, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Job Description

The Seller Experience team is the glue of our product ecosystem. We are the team that thinks outside of individual products and focuses on the entire experience a seller has in evaluating, signing up for, and using Square. The Seller Experience team is responsible for many of the shared surface areas and platforms that Square's products feed into, such as our public website (, sign-up and onboarding flows, dashboard, setup guides, support channels, and chatbots. We build and pave the sellers' path to getting value from our vast ecosystem of products and services. Our mission is to unify, personalize, and support seller experiences across Square.

We are looking for a Senior Conversation Designer to join the Seller Experience team. Working across multiple touch points and surfaces, you’ll:

  1. create a cohesive, conversational, and interactive chat experience for sellers across Square’s ecosystem 
  2. provide UX writing deliverables across other Seller Experience teams. 

You’ll also define a scalable conversation design workflow for internal use. And, as Square adopts and implements emerging artificial intelligent technologies, you’ll play a key role in helping us define our vision and accelerate our transition. You’ll also be on point to pitch in with UX writing deliverables across other Seller Experience teams. 

Conversation design deliverables and expectations:

  • Define and drive the overall conversational UX of our chatbots, in collaboration with subject matter experts, content writers, product managers, and other partners across Square
  • Design conversational touch points such as greetings, transitions, proactive notifications, and hand-offs—balancing multiple constraints, goals, and stakeholders to create a smooth seller experience
  • Review existing conversational UX and identify opportunities for improvement with clear rationale, including both quick wins as well as long term goals
  • Plan for, strategize, and evangelize ways to implement emerging technologies such as GPT-3 and other ML-driven dialogue models
  • Act as lead editor for all chatbot content, ensuring that a cohesive, conversational, interactive experience emerges from our many flows
  • Mentor and coach chatbot writers, helping them upskill in conversation design principles to improve content drafts, structure content platforms, and unify voice and tone
  • Collaborate within product teams as well as go-to-market teams—assess and prioritize opportunities, constraints, and features—advocating for the end user while balancing priorities and business goals
  • Work closely with data scientists and leverage quantitative and qualitative data as well as user feedback to drive and influence conversation design
  • Model how to use human-centered design approaches to frame problems, uncover patterns, discover opportunities, and visualize possibilities
  • Establish an ongoing process for managing and growing a sophisticated and flexible conversation design practice that adjusts to varying cycles and user demands

Content design deliverables and expectations:

  • Be hands on—designing, writing, and editing content across several teams within Seller Experience. This includes the smallest microcopy to the most visible content and everything in between.
  • Work embedded in design teams as a driver of content-informed design. Collaborate in Figma and have an active voice in design critiques. Use your content design knowledge to tease out design flaws and derive elegant solutions.
  • Drive best practices for content design in collaboration with our design systems team as well as other content designers across the company
  • Build strong relationships with cross-functional team members and effectively speak to processes and value of the writing discipline
  • Help the product design teams become more efficient by developing processes and workflows for collaboration
  • Apply metrics, data, design research, user testing, customer support insights, and more to inform content and language decisions
  • Manage and prioritize your workload of multiple projects with different collaborators


  • 5-7+ years of experience as a conversation designer, chatbot writer, UX designer, or content designer in highly collaborative, cross-functional environments
  • Strong writing and language skills, as an added bonus, but not required - an understanding of language models, taxonomies, linguistic principles, and AI/ML-driven conversations
  • Experience with and/or deep curiosity for linguistics and NLP, customer intent recognition, human-centered design, interaction design, information architecture, user research, and/or content design
  • Ability to design conversational dialogue that scales across locales and languages
  • Training, either formal or on-the-job, in design, computer science, information sciences, psychology, human factors, human-computer interaction, or a related field
  • Strong communication and presentation skills as well as the ability to organize and implement requirements from multiple cross-functional teams

Additional Information

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A: USD $202,500 - USD $247,500
Zone B: USD $192,400 - USD $235,200
Zone C: USD $182,300 - USD $222,800
Zone D: USD $172,200 - USD $210,400

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information. 

Benefits include the following:

  • Healthcare coverage
  • Retirement Plans including company match 
  • Employee Stock Purchase Program
  • Wellness programs, including access to mental health, 1:1 financial planners, and a monthly wellness allowance 
  • Paid parental and caregiving leave
  • Paid time off
  • Learning and Development resources
  • Paid Life insurance, AD&D. and disability benefits 
  • Perks such as WFH reimbursements and free access to caregiving, legal, and discounted resources 

This role is also eligible to participate in Block's equity plan subject to the terms of the applicable plans and policies, and may be eligible for a sign-on bonus. Sales roles may be eligible to participate in a commission plan subject to the terms of the applicable plans and policies. Pay and benefits are subject to change at any time, consistent with the terms of any applicable compensation or benefit plans.

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace.

Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. 

Learn more about our efforts to promote inclusion and diversity at

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis. 

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

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