Head of Sales Engagement Strategy

  • Full-time
  • Alternate Location: New York, United States

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

Square’s fast-paced Sales and Account Management (SAM) Enablement & Productivity team has an infectiously positive attitude and we are committed to win. We are looking for an experienced leader to become the Head of Sales Engagement Strategy. In this role, you will lead a global team responsible for partnering with Sales, Marketing, Product, and Enablement team members to develop the strategies and processes our sales representatives use each time they interact with prospects from first contact to closing the deal. You will play an integral role in optimizing the methods, channels, strategies, messaging, and content used to interact with prospects as they move through the sales pipeline and beyond to post sales account management. You will report directly to Global Head, Sales Enablement & Productivity.

You will:

  • Lead a team of sales engagement specialists to develop and execute sales engagement strategies that improve conversion rates, drive revenue growth, and increase customer loyalty globally.
  • Develop and execute a comprehensive sales engagement program that includes strategies, tactics, and tools for engaging with prospects and customers.
  • Work collaboratively with sales leadership, marketing, product marketing, and account management teams to understand business needs and develop sales engagement strategies that meet those needs.
  • Develop and maintain a library of sales engagement content, including email templates, pitch decks, product overviews, case studies, and testimonials that support the efforts of the sales team.
  • Manage the implementation and adoption of sales engagement tools, including outreach platforms (Salesloft) and content management systems (Seismic), to improve sales team productivity and effectiveness.
  • Monitor and report on the effectiveness of the sales engagement program, and make recommendations for improvements based on data-driven insights.
  • Partner with sales leadership to develop and implement sales engagement performance metrics and use data to measure the impact of sales engagement efforts on business outcomes.
  • Stay up-to-date with the latest trends, tools, and best practices in sales engagement and leverage this knowledge to continuously improve the program.


You have:

  • Masters degree or equivalent experience in Business, Marketing, or related field.
  • 5+ years of experience in sales engagement, sales enablement, sales operations, product marketing or related roles.
  • 3+ years of direct experience leading and developing teams.
  • Experience with developing and executing sales engagement strategies and tactics.
  • Strong project management skills, with experience managing multiple projects simultaneously.
  • Excellent communication and interpersonal skills, with the ability to work collaboratively across teams.
  • Strong analytical skills, with the ability to measure the impact of sales engagement efforts on business outcomes.
  • Familiarity with sales automation, outreach platforms, and content management systems.

If you have a passion for sales engagement and the ability to develop and implement effective strategies that drive revenue growth, we encourage you to apply for this position.

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 $184,100 - USD $225,000
Zone B: USD $171,200 - USD $209,200
Zone C: USD $162,000 - USD $198,000
Zone D: USD $152,700 - USD $186,700

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.

Privacy Policy