Full-Time

Deal Desk Senior Analyst

Posted on 8/21/2026

Twilio

Twilio

5,001-10,000 employees

Cloud communications platform with APIs

Compensation Overview

CA$68.2k - CA$85.2k/yr

+ 10% target bonus

Remote in Canada

Remote

Occasional travel may be required for project or team in-person meetings.

Bachelor's, Associate's

Category
Finance & Banking (1)
Required Skills
Financial analysis
Tableau
Salesforce
JIRA
Excel/Numbers/Sheets
Financial Modeling

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Requirements
  • A Bachelor's or Associate's Degree plus a minimum of 2 years of experience in Corporate Finance, Financial Planning & Analysis (FP&A), Commercial Finance, or an analytical Go-to-Market/Deal Desk role. If no degree, a minimum of 4 years of relevant analytical experience is required.
  • Demonstrated analytical and financial skills, with a firm understanding of core financial concepts and the ability to explain financial tradeoffs clearly.
  • Advanced Excel and Google Sheets skills, with proven experience building intermediate financial models, logic formulas, and scenario analyses.
  • The ability to manage multiple high-velocity requests simultaneously while remaining extremely organized under tight deadlines.
  • The ability to operate independently, ask clarifying questions, and work with high integrity.
Responsibilities
  • Analyze deal economics for standard and non-standard agreements, evaluating pricing, discounting, term length, usage commitments, and gross margin impact.
  • Partner with Sales to structure commercially sound deals by analyzing tradeoffs across price, volume, and risk, ensuring all structures align with Twilio's financial guardrails.
  • Build, maintain, and review financial models and pricing scenarios to support non-standard deal requests and senior leadership approval decisions.
  • Own the end-to-end Deal Desk operational workflow in Salesforce and CPQ, from quote building and pricing approvals to Order Form creation, DocuSign execution, and opportunity closure, ensuring data integrity and policy compliance.
  • Establish working relationships across Commercial Legal, Billing Operations, Corporate Finance, and Sales to streamline deal velocity, particularly during high-volume month-end and quarter-end peaks.
  • Act as a guardrail and educator for Sales and Go-to-Market teams, ensuring adherence to internal contracting policies, approval matrices, and discount governance.
  • Collaborate with Sales and Legal to review and structure non-standard contract language within Order Forms, ensuring alignment with corporate risk and revenue recognition policies.
  • Surface recurring deal patterns, approval exceptions, and operational friction points to contribute to the continuous improvement of Deal Desk workflows and system efficiencies.
Desired Qualifications
  • Knowledge and/or experience using online sales and document management tools such as Salesforce, Tableau, Contract Lifecycle Management (CLM), and Jira.

Twilio provides a cloud communications platform that offers APIs to add voice, messaging, video, and email into software applications. Developers use these APIs to build and scale communication features directly inside their apps. The product works by making it easy to program communications: you send calls or messages through API requests, manage video sessions, and integrate email, all on a pay-as-you-go basis that scales with usage. Twilio stands out from competitors by focusing on developer-friendly APIs that cover multiple channels in one platform, supporting customers from startups to large enterprises with global reach and optional consulting services. The company’s goal is to help any business communicate with customers at scale by providing reliable, programmable communications across channels.

Company Size

5,001-10,000

Company Stage

IPO

Headquarters

San Francisco, California

Founded

2008

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 revenue reached $1.50 billion, rising 22% year over year.
  • Management raised 2026 organic revenue growth guidance to 13%-13.5% on August 6.
  • Free cash flow hit $353 million, while share repurchases totaled $66 million.

What critics are saying

  • Guidance still implies 2026 revenue growth slowing to 18%-18.5%, below Q2's 22%.
  • Amazon, Google, and Microsoft bundle competing communications APIs into larger cloud contracts.
  • If AI agents bypass Twilio's channels, its moat collapses into commoditized plumbing.

What makes Twilio unique

  • Twilio's May 2026 Console unifies messaging, voice, email, Segment, and AI workflows.
  • Its May 2026 platform adds Conversation Memory, Orchestrator, Intelligence, and Agent Connect.
  • Twilio's 4,800 carrier connections and telecom compliance expertise remain hard to replicate.

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Benefits

Vacation: Twilio offers generous annual time off in all countries for you to enjoy.

Healthcare: We are dedicated to helping our employees live longer and healthier lives through comprehensive health programs.

Retirement: Twilio cares about your retirement! We offer programs to help our employees plan for their retirement needs.

Family leave: At Twilio we recognize the importance of family. We offer generous maternity, paternity, and adoption leaves, as well as family medical care leave.

Earn your stripes: Build and present a Twilio app to earn your Twilio track jacket and receive $30 per month for e‑books for continued learning and education.

Catered meals: We provide a variety of snacks, drinks, and catered meals in each of our locations.

Growth & Insights and Company News

Headcount

6 month growth

-7%

1 year growth

-7%

2 year growth

-7%
Yahoo Finance
Aug 13th, 2026
Twilio director sells 500,000 shares worth $123.5M after stock surges 159%

Andrew Stafman, Director at Twilio, sold approximately 500,000 shares of Class A Common Stock on 12 August 2026 for $123.5 million, according to an SEC Form 4 filing. The transaction represents a 79% reduction in his holdings. The shares were sold at a weighted average price of $247.08 per share, following a 159% stock price appreciation over the preceding 12 months. The shares were held through various entities including Sachem Head Capital Management LP, with Scott Ferguson and Andrew Stafman sharing potential beneficial ownership. Following the sale, Stafman retains approximately 133,000 shares across direct and indirect accounts, representing roughly 0.088% of Twilio's outstanding shares. Twilio provides cloud-based communications platforms through APIs, serving customers ranging from startups to Fortune 500 companies.

Yahoo Finance
Aug 6th, 2026
Twilio's Q2 revenue jumps 22% to $1.5B, stock surges 15.7%

Twilio reported second-quarter results that exceeded expectations, with revenue up 22% year on year to $1.50 billion, beating analyst estimates of $1.43 billion. The customer engagement platform's non-GAAP profit of $1.47 per share surpassed consensus estimates by 11.1%. The company's third-quarter revenue guidance of $1.51 billion came in 3.2% above analyst expectations. Operating margin improved to 5.6%, up from 3% in the same quarter last year, whilst free cash flow margin rose to 23.5% from 9.4% the previous quarter. Following the results announcement, Twilio's stock jumped 15.7%. The company's net revenue retention rate increased to 116%, up from 114% in the prior quarter.

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Jul 16th, 2026
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For the first time in human history, a rich understanding of language is available as a utility, delivered via API, useful enough to “be metered”. Intelligence has become a tool: something you can call, compose, and build on, divorced from any individual human mind.

FinSMEs
Jul 15th, 2026
Rime Raises $24M in Series A Funding

Rime, a San Francisco, CA-based provider of an enterprise voice AI platform, raised 24M in Series A funding

Yahoo Finance
Jul 14th, 2026
NICE vs Twilio: Profitability or growth potential in customer engagement tech

NICE and Twilio both serve the customer interaction technology market, but differ significantly in profitability and growth profiles. NICE, which provides AI-powered customer experience and financial compliance software, reported fiscal year 2025 revenue of nearly $2.9 billion, up 7.7% year-on-year. The company achieved net income of approximately $612.1 million with a 20.8% net margin. It maintains zero debt and generated free cash flow of roughly $622.8 million. Twilio offers developer tools for building messaging, voice, and email capabilities. Its fiscal year 2025 revenue grew 14% to nearly $5.1 billion. The company turned profitable with net income of approximately $33.8 million and a 0.7% net margin. Twilio generated free cash flow of approximately $1.0 billion whilst maintaining a low debt-to-equity ratio of 0.1x. NICE offers established profitability, whilst Twilio presents higher revenue growth potential.