Deal Strategist in Canada

GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50 million registered users and more than 50% of the Fortune 100* trust GitLab to ship better, more secure software faster. The same principles built into our products are reflected in how our team works: we embrace AI as a core productivity multiplier, with all team members expected to incorporate AI into their daily workflows to drive efficiency, innovation, and impact. GitLab is where careers accelerate, innovation flourishes, and every voice is valued. Our high-performance culture is driven by our values and continuous knowledge exchange, enabling our team members to reach their full potential while collaborating with industry leaders to solve complex problems. Co-create the future with us as we build technology that transforms how the world develops software. * Fortune 500® is a registered trademark of Fortune Media IP Limited, used under license. Claim based on GitLab data. Fortune 100 refers to the top 20% ranked companies in the 2025 Fortune 500 list, published in June 2025. Fortune and Fortune Media IP Limited are not affiliated with, and do not endorse products or services of GitLab. An overview of this role The Pricing team defines and executes GitLab's pricing strategy, a function that's important to our success. As a Lead Pricing Strategist, you'll shape pricing and packaging across our portfolio, from the Premium and Ultimate tiers to GitLab Duo and our growing set of artificial intelligence (AI) and usage-based products, including Flex and Orbit. You'll work with leaders across Product Management, Product Marketing, Finance, go-to-market teams, Sales, and Deal Desk to evaluate opportunities, create business models for new offerings, and improve how we package our existing portfolio. What you’ll do Collab

As Sigma scales its global footprint, the Sales Engineering (SE) organization is the technical engine driving our GTM motion. We are looking for a Strategy and Operations Lead, SE to partner directly with our VP of SE and serve as the operational bedrock for this critical organization. Operating within our broader GTM Strategy & Operations team, you will own the global operating rhythm, operational infrastructure, and capacity planning for the entire SE organization. You will drive strategy across a highly matrixed, global environment. You are part strategist, part builder, and part operator - responsible for ensuring our pre-sales motion scales seamlessly. What You Will Do Drive Business Reporting & the SE Operating Rhythm: Own the cadence of the SE organization. Design and execute regular business reviews and leverage Sigma to build robust, real-time reporting that gives the VP of SE crystal-clear visibility into technical pipeline health, team utilization, and conversion metrics. Optimize Funnel Mechanics & Deal Acceleration: Deep dive into the pre-sales funnel to identify where deals stall during technical validation. Partner with SE leadership to optimize the Proof of Concept (POC) lifecycle, remove friction, and accelerate the technical win. Lead Global Headcount & Capacity Planning: Serve as the SE representative in cross-functional GTM planning cycles. Own end-to-end global SE capacity requirements, design territory allocation frameworks, and manage annual headcount planning seamlessly across AMER, EMEA, and APAC. Build Solutions in Sigma: Leverage Sigma itself to build robust operational solutions, designing the dashboards, data models, and workflows needed for POC tracking, capacity management, and performance visibility. Act as the Cross-Functional Hub: Represent the SE organization in all major GTM Strategy & Operations initiatives. Serve as the connective tissue between SE, Sales, Product, and RevOps, ensuring SE requir

We're transforming the grocery industry At Instacart, we invite the world to share love through food because we believe everyone should have access to the food they love and more time to enjoy it together. Where others see a simple need for grocery delivery, we see exciting complexity and endless opportunity to serve the varied needs of our community. We work to deliver an essential service that customers rely on to get their groceries and household goods, while also offering safe and flexible earnings opportunities to Instacart Personal Shoppers. Instacart has become a lifeline for millions of people, and we’re building the team to help push our shopping cart forward. If you’re ready to do the best work of your life, come join our table. Instacart is a Flex First team There’s no one-size fits all approach to how we do our best work. Our employees have the flexibility to choose where they do their best work—whether it’s from home, an office, or your favorite coffee shop—while staying connected and building community through regular in-person events. Learn more about our flexible approach to where we work. Why this role is on the menu Instacart's Strategic Finance team partners across the business to drive disciplined growth and long-term value creation. Within this group, the Retailer pod supports our Retail Partnerships organization as we expand and deepen relationships with grocers and retailers across North America. In this role you will be the finance lead for retailer deal flow—setting financial strategy, shaping pricing philosophy, and driving portfolio-level decision-making across the full lifecycle of retailer partnerships. You will develop decision frameworks, build robust models, and advise senior leaders through high-stakes negotiations that shape Instacart’s revenue and margin profile. This is an individual contributor role to start, with a clear path to people management as the team grows. This person will report to the Director of Retailer Finan

Owns day-to-day deal pricing execution for Enterprise, including pricing calculations, staffing inputs, and dashboard reporting that gives Sales and Deal Desk leadership visibility into deal status, pricing, and margin. Partners with the Deal Desk Manager on customer deal structuring and on identifying ways to accelerate the deal approval process. What You’ll Do Deal Pricing Execution Manages day-to-day deal pricing calculations for Enterprise deals, including ROI modeling and EPD staffing inputs Applies existing pricing frameworks consistently across Land, Expansion, and Framework deals Partners with the Deal Desk Manager to design customer-specific deal structures for non-standard or complex deals Pricing & Deal Status Reporting Builds and maintains a pricing dashboard tracking deal status, pricing, margin, and overall deal health across the Enterprise pipeline Updates pricing and trend reporting to keep leadership current on where deals stand and how pricing is trending against targets Process Optimization Identifies bottlenecks in the deal review & approval process and proposes ways to accelerate cycle time Helps standardize and streamline recurring pricing/approval steps into repeatable, lower-friction workflows Tracks deal approval cycle time and surfaces trends to inform process improvements Cross-Functional Deal Coordination Owns deal crafting end-to-end from initial pricing/modeling through contract review, coordinating with sales management, reps, and internal stakeholders Ensures the relevant stakeholders (Accounting, Finance, EPD, Legal) review and approve deals at the appropriate stage before they progress Routes deal packages to the correct reviewers and tracks open items so deals aren't stalled waiting on sign-off Strategic & GTM Support Tackles ambiguous, open-ended questions around Scale's go-to-market motion and iterates quickly on solutions that deliver measurable results Supports Sales and Finance leadership in quarterly strategy and

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The Strategic Partnerships team develops and manages relationships with large partners that enable Stripe's product strategy and deliver new capabilities to Stripe users. Our team executes on high-impact, cross-functional initiatives across new products, geographic expansion, user advocacy, and policy. These partnerships have a significant impact on Stripe and the products used by millions of our users. We're looking for a senior member to join our team to develop new partnerships with our largest users and strategic partners, and drive critical initiatives that will be foundational for Stripe. A successful candidate will have significant experience delivering complex deal work, creating and driving strategy, working with cross-functional teams to launch new initiatives, and initiating first-of-a-kind partnerships. We're looking for someone who exhibits a strong sense of ownership, performs at a senior level, drives to have an impact, and has an entrepreneurial spirit. What you’ll do Responsibilities Evaluate and develop the business case to support Stripe’s product and engineering investment in new strategic partnerships across verticals (e.g. AI, Platforms, Payment Methods) Manage strategic planning, negotiation and new partnership development Ensure highly structured, methodical deal management rooted in milestones, KPIs, and alignment with partners on opportunities of mutual interest Navigate the largest partners, in partnership wi

We're transforming the grocery industry At Instacart, we invite the world to share love through food because we believe everyone should have access to the food they love and more time to enjoy it together. Where others see a simple need for grocery delivery, we see exciting complexity and endless opportunity to serve the varied needs of our community. We work to deliver an essential service that customers rely on to get their groceries and household goods, while also offering safe and flexible earnings opportunities to Instacart Personal Shoppers. Instacart has become a lifeline for millions of people, and we’re building the team to help push our shopping cart forward. If you’re ready to do the best work of your life, come join our table. Instacart is a Flex First team There’s no one-size fits all approach to how we do our best work. Our employees have the flexibility to choose where they do their best work—whether it’s from home, an office, or your favorite coffee shop—while staying connected and building community through regular in-person events. Learn more about our flexible approach to where we work. Overview Instacart’s Strategic Finance team partners closely with leaders across the business to drive clarity, rigor, and results. Within this group, the Retailer Pod supports our retailer partnerships by shaping deal strategy, building robust financial models, and guiding decisions that help Instacart and our partners grow together. We are seeking a Senior Financial Analyst to accelerate retailer deal flow and portfolio performance. You will join a high-impact, collaborative pod within Strategic Finance, working daily with Retail Partnerships, Deal Desk, Legal, Revenue Operations, Data Science, and Accounting. In this role, you’ll own end-to-end financial analysis for complex commercial deals, build scalable forecasting frameworks, and present actionable insights that influence decisions at the highest levels. This is an opportunity to roll up your

Strategic Commercial Account Executive About This Role This is one of the most critical positions at Sigma. The success of our business depends on bringing in the right customers, at the right stage of their growth, and this role focuses on the Mid Market accounts at the center of that effort. The right candidate will have the rare ability to open doors at the highest levels, navigate complex organizations, and drive deals that change the trajectory of both our customers’ businesses and ours. Sigma is growing at over 80% year over year, and this role is an opportunity to be at the forefront of that momentum. You’ll work directly with some of the best leaders in the industry, learning how to build relationships, influence decisions, and close transformative deals. If you succeed here, you won’t just have a great job—you’ll have a career-defining experience where you will earn your sales MBA. This role is based in San Francisco and is critical to the success of our business. It is not a remote position—you will be in the office four days a week, working side by side with some of the best in the industry. This is not just about being present; it’s about being immersed in a fast-moving environment where decisions are made, deals are won, and careers are built. Our office culture is passionate, collaborative, and rewarding. Travel: Travel is expected locally to the Bay Area and to the west coast 25% of the time. We encourage and do not limit in person meetings with prospects, customers, and partners. Who You Are: A high-impact, forward-thinking professional eager to drive innovation and shape the future of data-driven business strategy. A self-starter who thrives at a fast pace and takes ownership of big initiatives. Proven track record of multi-threading & navigating complex deal cycles with large ASP A strategic thinker who understands how data fuels transformation, decision-making, and competitive advantage. Runs value b

Our Enterprise Sales Executives target and close new business with Datadog’s largest, most strategic customers and prospects. In this role you’ll be focused on uncovering the pain points organizations face as they operate in or migrate to a cloud environment at scale as well as delivering the appropriate Datadog solution. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Prospect into large Fortune 1000 companies while running an efficient sales process Maintain, build and own specific relationship maps for your territory including existing relationships and aspirational contacts Develop a deep comprehension of customer's business Negotiate favorable pricing and business terms with large commercial enterprises by selling value and ROI Handle existing customer expectations while expanding reach and depth into assigned territory Demonstrate resourcefulness when faced with challenges that defy easy solution Have intuitive sense of necessary steps to close business and gain customer validation Identify robust set of business drivers behind all opportunities Ensure high forecasting accuracy and consistency Who You Are: Someone with 3+ years closing experience (mix of field selling within mid-market or enterprise) Driven and have met/exceeded direct sales goals of 1M+ and operated with an average deal size of $100k+ Able to demonstrate methodology to prospect and build pipeline on your own Experienced in working for an innovative tech company (SaaS, IT infrastructure or similar preferred) Experienced in selling into large Fortune 1000 companies with the ability to win new logos Role requires regular travel to client sites, within your area and other regions, using various modes of transportation (car, train, air), depending on business needs. Fluent

At Lyft, our purpose is to serve and connect. We aim to achieve this by cultivating a work environment where all team members belong and have the opportunity to thrive. We are looking for a high-impact Legal Operations Program Manager to join our expanding Legal Operations Team and sit at the center of our mergers & acquisitions (M&A) and post-close integration activity! This is a strategy-to-execution role that serves as the operating backbone for Legal across our most strategic transactions — owning legal integration execution in partnership with Lyft’s Corporate Development Integration Management Office (IMO), and the intake and governance layer that connects the Legal team to deal and integration work. The ideal candidate is tech-savvy, detail oriented, proactive, and able to drive outcomes across multiple concurrent transactions in ambiguous, high-stakes environments with a collaborative and transparent approach. Some key areas include: M&A integration program management, program leadership across concurrent initiatives, cross-functional and deal team engagement, outside counsel and vendor management across jurisdictions, legal entity management and governance, and building the repeatable operating model that scales Legal integration with company growth. This position reports to the Head of Legal Operations. As the company scales, the volume and complexity of strategic transactions — M&A, cross-border expansion, and new market entry — continues to increase. This role establishes a centralized operating model for Legal integration that ensures: Strategic transactions are executed with discipline, completeness, and a clear critical path Legal is embedded early and effectively, with strong planning-to-execution across multiple teams to deliver strong business results and manage risk The organization scales without accumulating operational, compliance, or technical debt Responsibilities: M&A Integration Program Management Own end-to-end legal in

About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The AI team is focused on one of Stripe’s most strategic growth areas: enabling the monetization and scaling of AI-native and AI-enabled businesses. We’re in a unique position – partnering with the world’s most ambitious AI companies (the likes of OpenAI, Anthropic, NVIDIA, etc) building on the frontier of artificial intelligence -- across infrastructure, foundation models, agents, and applications -- to help them grow and commercialize globally using Stripe’s full financial stack. As part of Stripe’s GTM / Sales organization, this team works closely with Product, Engineering, and Marketing to shape Stripe’s AI GTM strategy and ensure that the world’s leading AI companies -- from early-stage innovators to the largest public players -- choose Stripe as their monetization platform. What you’ll do Work with existing Stripe customers in the AI Industry to develop and execute long-term sales strategies to expand Stripe’s revenue Own the full sales cycle, from business case development, to deal structuring and negotiating, to close Develop account plans and cross sell into your list of strategic AI customers, driving growth through expansion and new revenue streams Drive deal strategy and commercial negotiations for large, complex renewals Develop relationships with executive stakeholders within your book of business, deeply understanding problems they are solving and helping drive to solutions Be responsible for account mapping and coordinating ef

At Scale, we believe that AI will dramatically improve the world, and our mission is to accelerate the development of AI. We’re looking for a Field Marketing and Events leader to continue to build and manage Scale’s robust Gen AI and Research field marketing and events program, including but not limited to Scale hosted executive events, Scale hosted practitioner events and meetups, research conferences, and our annual flagship conference, AI Leadership Summit. You will join a rapidly growing team with the opportunity to manage and execute events from start to finish, drive lead generation and pipeline growth, and plan event programming with the largest names in AI. The successful candidate will have a solid understanding of technology, model builder, and research markets, strong project management skills, a strategic mindset, ability to manage and grow a team, and a passion for AI & technology. You will: Own annual planning for all Gen AI and Research events including strategy and budget Establish event activities in line with sales goals and deal acceleration, prioritizing goals from the go-to-market leadership and business development teams on event location and audience Manage team of field marketing and events managers who will execute on planning and logistics. This role should have a player-coach mentality and ability to also execute on nuts to bolts planning for all executive dinners, meetups, happy hours, sponsored trade shows, and hosted conferences Manage contractor relationships including event production firms and outside vendors, and event budgets Align with growth marketing on marketing campaigns and marketing qualified lead (MQL) reporting Track event campaign performance, measuring ROI, results, and metrics through Salesforce and own any course correction for events that are not performing Own all aspects of Scale hosted conference, Scale AI Base Camp, including venue selection, vendor management, logistics, speaker

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The AI team is focused on one of Stripe’s most strategic growth areas: enabling the monetization and scaling of AI-native and AI-enabled businesses. We’re in a unique position – partnering with the world’s most ambitious AI companies (the likes of OpenAI, Anthropic, NVIDIA, etc) building on the frontier of artificial intelligence -- across infrastructure, foundation models, agents, and applications -- to help them grow and commercialize globally using Stripe’s full financial stack. As part of Stripe’s GTM / Sales organization, this team works closely with Product, Engineering, and Marketing to shape Stripe’s AI GTM strategy and ensure that the world’s leading AI companies -- from early-stage innovators to the largest public players -- choose Stripe as their monetization platform. What you’ll do Work with existing Stripe customers in the AI Industry to develop and execute long-term sales strategies to expand Stripe’s revenue Own the full sales cycle, from business case development, to deal structuring and negotiating, to close Develop account plans and cross sell into your list of strategic AI customers, driving growth through expansion and new revenue streams Drive deal strategy and commercial negotiations for large, complex renewals Develop relationships with executive stakeholders within your book of business, deeply understanding problems they are solving and helping drive to solutions Be responsible for account mapping and coor

At Lyft, our purpose is to serve and connect. We aim to achieve this by cultivating a work environment where all team members belong and have the opportunity to thrive. Lyft is seeking a seasoned People Business Partner with deep expertise in M&A to join our People Team. Reporting to the Senior Director of People Business Partners, this high impact Director role will be the strategic center of gravity for all People M&A work. Role & Responsibilities: Lead the People M&A Function: Serve as the senior People partner and decision-maker across the M&A lifecycle. Lead through influence across a matrixed environment, coordinating across a shared Project Manager, People Business Partners, and COE partners. Partner effectively with a dedicated Project Manager to delegate execution and workstream coordination, while maintaining clear ownership of People strategy, talent decisions, and integration outcomes. Define and drive People integration strategy as the dedicated advisor to the Integration Management Office (IMO). Flex into other high-priority areas of PBP or People Team initiatives as needed. Drive Due Diligence: Lead People due diligence efforts, assessing organizational culture, headcount structures, compensation and benefits gaps, employment contracts, and law exposure across geographies. Conduct or oversee talent assessment processes, evaluating leadership bench strength, key person dependencies, and retention risk. Partner with Corporate Development, Legal, and Finance to ascertain People risks, synthesize findings into clear deal recommendations, and inform decisions. Design & Execute Workforce Integration: Advise senior leadership on org design decisions arising from acquisitions, including role mapping, spans and layers, redundancy management, and leadership selection - connecting org decisions to Lyft's operating model and culture. Partner with People Business Partner and Peop

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. What you’ll do As an Account Executive, Existing Business, you’ll be managing existing relationships and identifying new opportunities to expand Stripe’s footprint within existing accounts. Specifically, we’re looking for someone who can execute on long-term sales strategies, engage with internal and external stakeholders, align on technical and business requirements with product teams, build value in competitive situations, lead commercial negotiations, and close deals. Responsibilities Work with existing Stripe customers to develop and execute long-term sales strategies to expand Stripe’s revenue Own the full sales cycle, from business case development, to deal structuring and negotiating, to close Develop account plans and cross sell into your list of strategic customers, driving growth through expansion and new revenue streams Drive deal strategy and commercial negotiations for large, complex renewals Develop relationships with executive stakeholders within your book of business, deeply understanding problems they are solving and helping drive to solutions Be responsible for account mapping and coordinating effective meetings with the appropriate external stakeholders expanding the customer relationship Lead and contribute to team projects to develop and refine our sales process and help shape the Stripe sales culture Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirem

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. What you’ll do As an Account Executive, Existing Business, you’ll be managing existing relationships and identifying new opportunities to expand Stripe’s footprint within existing accounts. Specifically, we’re looking for someone who can execute on long-term sales strategies, engage with internal and external stakeholders, align on technical and business requirements with product teams, build value in competitive situations, lead commercial negotiations, and close deals. Responsibilities Work with existing Stripe customers to develop and execute long-term sales strategies to expand Stripe’s revenue Own the full sales cycle, from business case development, to deal structuring and negotiating, to close Develop account plans and cross sell into your list of strategic customers, driving growth through expansion and new revenue streams Drive deal strategy and commercial negotiations for large, complex renewals Develop relationships with executive stakeholders within your book of business, deeply understanding problems they are solving and helping drive to solutions Be responsible for account mapping and coordinating effective meetings with the appropriate external stakeholders expanding the customer relationship Lead and contribute to team projects to develop and refine our sales process and help shape the Stripe sales culture Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirem