Sr. Deal Operations Lead, Sales

  • 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.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality through Afterpay, 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


Deal Structuring, Support and Execution: 

  • Develop and maintain a comprehensive understanding of the company’s products, services, and pricing strategies. 
  • Collaborate with sales and finance teams to structure complex deals that align with company objectives and customer needs. 
  • Act as trusted advisor to the sales team by providing deal support and guidance throughout the sales process. 
  • Review and validate sales proposals, contracts, and other deal-related documentation for accuracy, consistency, and compliance with company policies and guidelines. 
  • Work closely with legal, finance, credit risk, and other stakeholders to address contractual and business terms, negotiate agreements, and mitigate risks. 

CPQ Help Desk 

  • Serve as the primary point of contact for CPQ escalations and act as a help desk for sales team members. 
  • Address and resolve CPQ-related issues, questions, and challenges raised by AEs and AMs in a timely and efficient manner. 
  • Provide hands-on support and troubleshooting for Salesforce CPQ system, including configuration, pricing rules, quoting templates, and approval processes. 
  • Stay updated on new features and updates within Salesforce CPQ and communicate relevant information to the sales team. 

Process Improvement and Optimization 

  • Identify opportunities to streamline and improve the deal desk and quote to cash processes, including workflow automation, documentation standardization, and knowledge sharing initiatives. 
  • Implement best practices and ensure adherence to sales policies, procedures, and compliance requirements, including guidance on Salesforce CPQ functionalities.  
  • Continuously monitor and analyze deal performance metrics, providing insights and recommendations to optimize sales effectiveness and deal outcomes. 
  • Actively participate in testing and implementation of system enhancements or new CPQ functionalities. 

Cross-Functional Collaboration 

  • Act as the primary liaison between the sales team and other cross-functional teams involved in the quote to cash process. 
  • Collaborate with IT and other technical teams to resolve any system-related issues or bugs impacting the quote to cash process. 
  • Partner with Enablement to create and maintain documentation, training materials, and knowledge base articles to assist users in utilizing CPQ effectively. 
  • Collaborate with internal stakeholders to gather user requirements and provide input for CPQ system enhancements or customizations.


You will have: 

  • Minimum of 5 years of experience in an enterprise-level role within the SaaS/B2B industry, with a focus on Deal Desk, Order Management, Finance Operations, Sales Operations, or Pricing.
  • Excellent communication and interpersonal skills, with the ability to effectively collaborate with cross-functional teams and influence stakeholders at various levels.
  • Proven track record of successfully partnering with go-to-market (GTM) teams and cross-functional systems teams to drive operational excellence and achieve business objectives.
  • Basic understanding of revenue recognition rules and their impact on deal structures and pricing decisions.
  • Highly organized with a strong attention to detail, ensuring accuracy and precision in deal documentation and processes.
  • Customer-focused mindset, always seeking to understand and meet the needs of internal stakeholders and external customers.
  • Innovative thinker with a creative approach to problem-solving and process improvement.
  • Self-aware, transparent, professional, and open to feedback, fostering a collaborative and constructive work environment.
  • Ability to multitask and prioritize effectively, particularly during high-volume periods and at the end of month or quarter.
  • Strong ability to prioritize tasks and manage distractions, maintaining focus on critical objectives.
  • In-depth knowledge and understanding of a CPQ (Configure, Price, Quote) tool, such as Salesforce CPQ, Apttus (Conga) CPQ, etc.

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 $125,600 - USD $153,600
Zone B: USD $119,300 - USD $145,900
Zone C: USD $113,000 - USD $138,200
Zone D: USD $106,800 - USD $130,600

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. 

Full-time employee benefits include the following:

  • Healthcare coverage (Medical, Vision and Dental insurance)
  • Health Savings Account and Flexible Spending Account
  • 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 (including 12 paid holidays)
  • Paid sick leave (1 hour per 26 hours worked (max 80 hours per calendar year to the extent legally permissible) for non-exempt employees and covered by our Flexible Time Off policy for exempt employees) 
  • Learning and Development resources
  • Paid Life insurance, AD&D, and disability benefits 
  • Additional Perks such as WFH reimbursements and free access to caregiving, legal, and discounted resources 

These benefits are further detailed in Block's policies. 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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