• Deliver targets for bookings, on-time renewals, net revenue retention, and multi-suite expansion by creating and executing sales plays within an assigned territory of accounts. • Build and refresh quarterly territory plans tied to whitespace, executive personas, funded initiatives, services attach, adoption gaps, and next plays by buying persona. • Create and progress pipeline by running named plays, executive outreach, and multi-threaded engagement across Superintendent, CIO, CFO, CHRO, CAO, Procurement. • Run deals end to end from discovery through close, including RFP strategy, pricing and terms, commercial approvals, legal negotiation, and procurement timeline control. • Maintain forecast accuracy and CRM standards, including contacts, activities, next steps, and stage exits that map to PowerSchool’s standard deal methodology. • Orchestrate Solution Consulting, Services, Customer Success, and Partners to drive value realization, run QBRs, meet SLAs, and renewal readiness. • Capture and relay market signals and customer feedback to product, pricing, and go-to-market teams to improve offer structure, sales plays, or guidance for product, pricing, and marketing. • Travel regularly (50–60%), including multi-state trips, to support high-impact initiatives such as advancing strategic deals, leading onsite demos, and facilitating executive workshops, especially during peak business cycles.

• Needs analysis & consultation • Outbound telephone contact (warm leads) • Relationship building & appointment scheduling

Role Description You’ll own the western region as our Senior Account Executive, Programmatic. That means building and converting a pipeline of high-value brands and agencies, running a consultative sales motion anchored in real data, and serving as the commercial face of 2045 on the West Coast. This is not a volume role. Our deal floor is $15K CAD/month and our clients expect senior-level thinking from the first conversation. You’ll have everything you need to deliver that. You must be located on the West Coast of the US or Canada. What You’ll Do - Own and grow the programmatic sales pipeline across Western Canada and the US West, focused on high-ACV, high-intent accounts in verticals including Media & Entertainment, Retail, Financial Services, Travel, Government, Pharma, Auto, and CPG. - Lead consultative, account-based sales conversations, positioning our Non-Price Variables™ (efficacy, agility, consistency, expertise) rather than competing on media cost. - Develop and convert relationships with senior stakeholders at independent agencies, D2C brands, eCommerce companies, and client-direct accounts. - Collaborate with our internal data scientist and trading team to build custom, insight-led proposals that are impossible to ignore. - Leverage our Diamond-Shaped Campaigns™ methodology and multi-DSP infrastructure to differentiate in every pitch. - Maintain disciplined pipeline hygiene in HubSpot and participate in weekly revenue reviews with the CRO. - Represent 2045 at key industry events and build your regional presence as a trusted, senior programmatic voice. Qualifications - Must have proven track record in programmatic advertising sales, whether from agency, DSP, SSP, or independent AdTech. - Demonstrated ability to close high-value, complex deals and manage multi-stakeholder sales cycles. - Deep fluency in programmatic mechanics: DSPs, PMPs, audience targeting, measurement, and attribution. - A consultative, strategic approach. You lead with insight, not rate cards. - Strong relationship builder who earns trust at the senior level and knows how to entertain, educate, and close. - Comfort working in a lean, high-accountability environment where your results are visible and your ideas get heard. - Experience across multiple client types: independent agencies, holding company groups, and brand-direct. Benefits - Flexibility That’s Real: One day per week in-office. The rest is yours to manage. We trust you to own your time because we hire people who own their outcomes. - Benefits From Day One: Full benefits package starts on your first day. We don’t make you wait 90 days to feel valued. - Vacation + Personal Days, No Guilt: Burned-out AEs don’t close deals. Rested, sharp ones do. Take the time. - AI-Forward Culture: Everyone at 2045 is Google AI Professional certified. You’ll have tools, training, and a team that thinks about AI as a competitive advantage, not a buzzword. - Direct Impact and Visibility: Your ideas won’t die in committee. Your wins get celebrated with the full leadership team. This is build-mode. - Clients Worth Working For: Ambitious brands focused on outcomes. No babysitting. No vanity metrics. Real work with real stakes.

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, 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. The Role As an Enterprise Account Executive you will lead Square's expansion into the country's most strategic sellers. This is a high-impact role for a proven enterprise seller who can identify the right opportunities, build strong executive relationships, and drive complex deals from first engagement through launch. You will own accounts end-to-end-setting account strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups with urgency. You'll partner closely with Solutions Engineering, Product, Partnerships, Legal, and Finance to bring the full Square ecosystem to market. We're looking for someone who combines strong commercial judgment with disciplined execution, and who raises the bar on how enterprise deals are run. You Will - Own a targeted set of enterprise accounts Set clear priorities and be accountable for pipeline quality, deal progression, and closed revenue across your account set. - Define and execute a clear account strategy Focus on the highest-impact opportunities and consistently convert pipeline into high-value wins. - Lead complex, multi-stakeholder deals end-to-end Navigate executive, technical, and commercial stakeholders to drive alignment, accelerate decisions, and close deals at pace. - Develop strong, insight-led account POVs Translate Square's platform into differentiated value that advances deals and improves win rates. - Run a disciplined, detail-oriented sales process Maintain momentum across long cycles, qualify rigorously, and increase conversion at each stage of the funnel. - Partner cross-functionally to win Work across Solutions Engineering, Product, Partnerships, Legal, and Finance to remove blockers and close complex deals effectively. - Represent Square with credibility at senior levels Build trusted relationships with executives that unlock access, influence decisions, and drive long-term partnerships. You Have - 8+ years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership - Proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgment on where to invest time and why - Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control - Strong commercial acumen, with the ability to structure and negotiate deals thoughtfully across pricing, scope, and long-term value - Executive presence and credibility-you communicate with precision, challenge constructively, and earn trust with senior decision-makers - Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations - A high standard for execution: you are disciplined, prepared, and follow through consistently, especially in long and ambiguous sales cycles - A strong sense of ownership-you take responsibility for outcomes, not just activity, and operate effectively without heavy structure - The ability to simplify complexity and drive clarity, both externally with customers and internally across teams 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 identity or 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. Block is a globally distributed company and this role will require working with other employees in multiple time zones. You may be required to perform work outside of normal business as part of this role Application Guidelines Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed. Use of AI in Our Hiring Process We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. Contact us here with hiring practice or data usage questions. Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block. Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we're helping build a financial system that is open to everyone.