Senior Engineering Manager, Conversations

  • Full-time

Company Description

Since we first opened our doors in 2009, the world of commerce has evolved immensely – and so has Square. After enabling anyone to take a payment and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, run a busy kitchen, book appointments, engage loyal buyers, and hire and pay staff. And 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 all in one place.

Today, we’re a partner to sellers of all sizes – large, enterprise-scale businesses with complex commerce operations, sellers just starting out, as well as merchants who began selling with Square and have grown larger over time. As our sellers scale, so do our solutions. We all grow together.

There is a massive opportunity in front of us. We’re building a business that is big, meaningful, and lasting. And we are helping sellers around the world do the same.

Job Description

The Conversations team at Square builds Square Messages and Square Assistant, aimed at facilitating commerce over messaging while saving sellers' time. We're integrated into Square's point of sale apps on Web, iOS, and Android; the team powers nearly all of Square's buyer-facing communication. The year ahead will see the team build out more inbound channels (e.g., a dedicated business line, web widgets, etc.) while building out more powerful automation and prioritization tools for upmarket businesses. 

As an Engineering Lead on the Conversations team, you will lead a multidisciplinary engineering team of 20 Backend, Web, iOS, Android and AI/ML engineers and engineering managers. You will represent your team across the organization, working closely with cross functional partners across design, product, marketing, data science and risk. You will go deep to understand the needs of businesses of all sizes and ensure our platform is architected to help any seller onboard and use our product successfully. You will work with your team to create remarkable seller-facing experiences and deliver an intuitive and extensible platform for internal stakeholders. This impactful and visible role requires a leader who can build a long-term vision for the space, drive execution, and establish credibility and influence across Square’s ecosystem of products. Sound like you? Read on.

You will...

  • Play a key role in building a messaging experience used by millions of sellers
  • Work with teams of engineering managers, engineers and product managers across the Square ecosystem to bring Square-wide capabilities into Messages
  • Help build out a new revenue line for Square
  • Work cross collaboratively with product managers and designers to help define and iterate on our product & engineering strategy 
  • Ship cutting-edge AI and features based on LLMs (large language models) to businesses that traditionally haven’t had access to it
  • Mentor engineers and managers and help cultivate their career aspirations



  • 8+ years relevant software development and systems design experience with hands-on engineering experience on large Backend systems or AI / ML systems
  • 4+ years of experience as a Software Development Manager; 2+ years managing managers. Experience managing staff or principal engineers. 
  • Experience with working on and managing teams that worked on and operated business critical distributed systems infrastructure
  • Experience effectively managing demanding stakeholders and partner relationships.
  • Technical to the point of having clarity with principal engineers and engineering leaders on architecture and engineering strategy decisions.
  • A good mix of process orientation and bias to action.
  • Skilled in collaborating across functions and possesses the abilities to think critically, communicate clearly, and make difficult decisions and tradeoffs either independently or in a coordinated manner.
  • Experience in building a team, defining its mission, and executing on its goals. Able to demonstrate going through the whole full lifecycle of recruiting, mentoring, and retaining great people that fulfill this mission.
  • A track record of achieving business and product success in a deeply collaborative organization where they are given a significant level of independence and accountability.

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 $269,600 - USD $329,500
Zone B: USD $269,600 - USD $329,500
Zone C: USD $269,600 - USD $329,500
Zone D: USD $269,600 - USD $329,500

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, veteran status, 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. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

Additionally, we consider qualified applicants with criminal histories for employment on our team, assessing candidates in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance.


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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