Director, Customer Success Data and Analytics Engineering på Toast i Boston
Toast · Boston
Director, Customer Success Data and Analytics Engineering
Role Overview
This role serves as the data leader and technical authority for Customer Success data at Toast. You will own the strategy and
execution of CS dat...
Role Overview
This role serves as the data leader and technical authority for Customer Success data at Toast. You will own the strategy and
execution of CS data modeling initiatives -- redesigning the CS data model from the ground up and defining how data is accessed,
queried, and served across the organization.
The CS data model needs to work reliably in two modes: as a structured foundation for dashboards, reporting, and operational
metrics, and as a well-documented, trustworthy layer that AI systems can query consistently. Building for both -- and making
deliberate architectural decisions about when each approach is appropriate -- is central to this role.
This is an embedded role, sitting inside the CS organization. CS data problems are business problems first -- understanding how
customers are being supported, where friction exists, and what patterns predict risk or opportunity requires close proximity to
the teams asking those questions. This role is positioned to build that context directly and translate it into data architecture
decisions.
You will lead a small team of two senior data and analytics engineers to start, with room to grow as the function matures.
What You'll Do
Data Architecture & AI Data Strategy
Own the redesign of the unified CS data model, connecting data across Care, CX, Enablement, and CSS teams and source systems
including our new contact center platform.
Define and execute the AI data strategy for CS -- specifically, how AI accesses, queries, and interacts with the data model.
This means making active architectural decisions about when to pre-calculate and structure data versus when to allow dynamic AI
retrieval, with predictability and consistency of outputs as the governing constraint.
Build and maintain a documentation layer that functions as a first-class artifact -- not an afterthought. Reliable AI data
access depends on well-structured, accurate documentation, and this person will treat it that way.
Develop and apply a clear framework for when AI is the right tool versus traditional data approaches. Part of the job is
pushing back when AI is unnecessary or introduces reliability risk.
Platform & Pipeline Development
Lead the data integration for the contact center platform migration, ensuring clean, well-modeled contact data flows into the
CS data layer from day one.
Design and optimize pipelines for analytics, reporting, and AI/ML-driven use cases.
Establish testing, monitoring, and alerting as standard practice across CS pipelines -- freshness checks, completeness
validation, anomaly detection. Stakeholders should never be the first to know something is broken.
Leadership & Cross-functional Partnership
Manage and mentor two senior data and analytics engineers, providing clear direction and building a high-performance team from
the ground up.
Serve as the primary data architecture partner for CS analytics and operations leaders, translating business problems into data
model and tooling decisions.
Collaborate closely with cross-functional peers in CS analytics, enterprise data infrastructure, finance, and business
technology to align on KPI definitions, data lineage, and governance standards.
Represent CS data interests in enterprise governance forums, ensuring security, compliance, and architecture standards are met.
Enablement & Governance
Ensure CS data is accurate, accessible, and trusted by the teams who depend on it -- from strategic OKRs down to operational
dashboards.
Maintain a shared KPI dictionary, data lineage map, and self-service analytics framework in partnership with centralized data
teams.
Establish clear SLAs for data delivery and processes for ongoing data quality monitoring.
What We're Looking For
Required Qualifications
10+ years of experience in data platform, data modeling, or analytics engineering roles, with at least 3 years in a leadership
capacity.
Experience designing data models with AI consumption in mind -- structuring for retrieval versus pre-calculation tradeoffs,
ensuring predictability of outputs, and understanding that documentation is infrastructure, not overhead.
Hands-on experience with modern data stack tools -- Snowflake, dbt, or equivalent -- including building or maintaining a
semantic layer that ensures consistent metric definitions across BI tools, notebooks, and AI agents.
A track record of treating pipelines like software: automated tests, schema validation, freshness and completeness monitoring,
and changes that go through review before they reach production. You have been burned by silent data failures and build
accordingly.
Proven ability to diagnose systemic data quality and architecture problems and redesign from the ground up -- not just patch on
top of what exists.
Strong cross-functional communication skills -- you can translate complex data architecture decisions for non-technical
business stakeholders.
Preferred Qualifications
Experience working in Customer Success, SaaS, or customer-facing operational analytics environments.
Familiarity with Snowflake and modern orchestration frameworks (dbt, Airflow, or equivalent).
Background that skews toward data modeling and transformation work -- you think in terms of data models, schemas, and semantic
layers rather than services and application infrastructure.
Experience with BI tools and dashboarding.
Familiarity with real-time data streaming technologies (Kafka, Kinesis, or equivalent).
Who Will Thrive Here
You are energized by greenfield work. This role is building something new, and the fingerprints you leave on the data model and
AI strategy will be visible and lasting.
You are comfortable with a lean team today. Two direct reports to start, with room to grow -- this is not a role for someone
who needs org size to feel impactful.
You have the judgment to advocate for the right use of AI, including knowing when not to use it. The goal is a trustworthy,
reliable data layer -- not AI for its own sake.
You are a builder first. Strategy matters, but so does the ability to roll up your sleeves and make decisions at the
implementation level.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and
geographic location. In addition to base salary, our total rewards components include cash compensation (overtime,
bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our
Geographic Pay Zone Philosophy.
Zone A
$217,000—$347,000 USD
Zone B
$188,000—$301,000 USD
Zone C
$170,000—$272,000 USD
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with
tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation.
Datadog's Technical Solutions (TS) organization is one of the largest organizations in the company — spanning Sales Engineers,
Technical Account Managers, Enterprise Customer Success Managers, Technical Support Engineers, and Solutions Architects who work
with prospects and customers across every stage of their journey with Datadog.
Technical Solutions Operations (TSO) exists to make that organization faster, smarter, and more scalable. We build the systems,
analytics & programs that give TS teams more leverage — and we measure our success by the business outcomes we drive, not the
projects we complete. The programs this team runs touch every function in TS, and the operating model you build will define how
that scales.
We're looking for a Director of Technical Program Management to lead the TSO Program Management team. This role sits at the
intersection of strategy and execution: you'll own the programs that shape how TS operates at scale, lead a team of technical
program managers, and serve as a peer to the Directors and VPs who run the teams you support. Your counterparts are leaders
overseeing hundreds of customer-facing technical professionals, and your role is to successfully interface with each organization
with proactive solutions on how your team can help them be more effective. This is a rare opportunity to lead a function where the
output isn't a deliverable, it's organizational capability. If you want to build something that compounds across an entire
organization, this is the role.
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
* Run the PMO as a business impact function. Own the PMO operating model end-to-end, including intake, prioritization, scoping,
execution, and impact measurement — with every program directly linked to measurable business outcomes such as productivity
gains, revenue influence, cost efficiency, or customer experience improvements. Establish a PMO operating standard that other
TS leaders adopt as the benchmark.
* Build capabilities that scale across TS, not point solutions. Build durable, cross-functional capabilities that drive business
outcomes across every function in TS. Solve systemic problems with scalable solutions and operating models — not one-off fixes
— and hold your team to the same standard.
* Drive programs from alignment to impact. Establish clear scope, sequencing, ownership, and success metrics before execution
begins. Hold your team to rigorous delivery standards and close every program with post-launch reporting that connects leverage
created directly to business outcomes for partner teams.
* Represent TSO in executive forums. Represent TSO in executive forums with Director and VP-level counterparts across TS. Come
prepared with clear recommendations, framed trade-offs, and the ability to drive decisions — not surface issues. Own
stakeholder relationships and outcomes and drive alignment across disparate teams.
* Deploy AI to create operational leverage. Identify and build AI-enabled workflows that reduce friction across how programs are
planned, communicated, and executed — for your team and for the TS functions you support. This is a core expectation, not a
future initiative. You bring a clear point of view on where AI creates a genuine capability shift and you build toward it.
* Develop the TPM team and raise the bar. Lead a team of senior Technical Program Managers delivering complex, concurrent
initiatives across TS. Raise the bar for execution quality, stakeholder management, and accountability — and develop a team
that operates independently and owns outcomes.
* Build cross-functional relationships before you need them. Build cross-functional relationships across TS and adjacent
functions before programs require it. Use influence, credibility, and direct engagement to drive alignment, resolve tension,
and expand the reach and impact of TSO well beyond its own boundaries.
WHO YOU ARE
* 10+ years running complex, cross-functional programs at a senior level, with VPs and senior Directors as your primary
stakeholders — ideally within a high-growth B2B SaaS go-to-market, customer-facing, or revenue operations organization
* A systems builder with a track record of designing operating models, playbooks, and frameworks that other teams adopted as a
reference standard
* Autonomously executive-ready — decisive under ambiguity, composed under pressure, and capable of leading VP-level conversations
without preparation coaching
* Experienced applying AI as an operational tool, with a practical point of view on where it creates capability shifts — not just
productivity gains
* A developer of senior talent who raises the bar on what great program management looks like and builds teams that operate
independently at a high standard
* Outcome-oriented and metric-driven — you define success before work begins and hold yourself and your team accountable to
delivering against it
PREFERRED EXPERIENCE
* Experience supporting large-scale go-to-market or customer-facing technical organizations spanning sales engineering,
post-sales, technical support, or solutions architecture
* Familiarity with support operations platforms and the workflows they enable across technical teams
* Experience designing org-wide AI-enabled capabilities in an operational context
* Background in tooling strategy, workforce planning, or operational transformation at scale in a SaaS environment
Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's
okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply.
Benefits and Growth:
* New hire stock equity (RSUs) and employee stock purchase plan (ESPP)
* Continuous professional development, product training, and career pathing
* Intradepartmental mentor and buddy program for in-house networking
* An inclusive company culture, ability to join our Community Guilds (Datadog employee resource groups)
* Access to Inclusion Talks, our Internal panel discussions
* Free, global mental health benefits for employees and dependents age 6+
* Competitive global benefits
Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.
To conform to US export control regulations, candidates should be eligible for any required authorizations from the US government.
This job is available in various departments within our company; to conform to US export control regulations, some of these roles
may require candidates to be eligible for any required authorizations from the US government.
Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on
factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class,
comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health
benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.
The reasonably estimated yearly salary for this role at Datadog is:
$224,000—$280,000 USD
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About Datadog:
Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the
technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place,
using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI
leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram,
LinkedIn, and Datadog Learning Center.
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Equal Opportunity at Datadog:
Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national
origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other
characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal
requirements. Here are our Candidate Legal Notices for your reference.
Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of
our website or need assistance completing the application process, please complete this form. This form is for accommodation
requests only and cannot be used to inquire about the status of applications.
Privacy and AI Guidelines:
Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and
Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.
PRINCIPAL, GTM STRATEGY (SALES BUSINESS PARTNER)
Location: US
Reporting to: VP, GTM Strategy & Operations
About the Role
You are a senior Individual Contributor (IC) who acts as the "Strategic Diplomat" and key partner to our Regional VPs of Sales.
You serve as the "connective tissue" between sales leadership goals and the technical Strategy & Operations engine, operating
within the strategic framework set by the VP. VPs love you because you understand their world, and you drive value by translating
their needs into data-driven strategy and automated solutions.
What You’ll Do
* Sales Business Partnering: Serve as a key strategic partner to the VPs, working in close alignment with the VP of GTM Strategy
& Operations. You attend leadership meetings and translate qualitative field needs into quantitative requirements for the S&O
team.
* Full-Funnel Oversight: You monitor the "Whole Number." You ensure VPs understand their retention benchmarks and have the data
needed to protect their base.
* Field Innovation Scout: You are a key bridge to the Innovation team. You identify the manual tasks VPs and reps are facing and
work with the Director of Insights and Innovation to scope the AI Agents required to address them.
* Specialized Executive Reporting: Own the "Last-Mile" reporting for Sales QBRs. You take core dashboards from the Insights team
and "story-tell" the data for VPs.
* Enablement Liaison: Partner with the VP of Enablement to ensure that when a new process or AI tool is "released," the VPs are
bought in and the coaching is aligned.
* Conflict Resolution: Support resolution of territory or quota disputes by preparing data-driven analyses and recommendations
for the VP to review and action.
What You Bring
* Experience: 8+ years in Sales Operations, GTM Strategy, or Revenue Operations roles.
* Executive Presence: Strong ability to partner with VPs and present data-driven recommendations while maintaining strong working
relationships.
* Generalist Mastery: You are a "Sales Ops Hero" who can think across Sales, CS, Marketing, and Finance datasets.
* Operational Grit: Willingness to get into the weeds to solve a VP's problem while having the discipline to hand off the
long-term solution to the Pune COE.
About Showpad
At Showpad, we’re focused on empowering others to be at their best. As a global leader in AI-powered revenue effectiveness, we
provide revenue teams with the platform they need to prepare sellers, engage buyers, and drive predictable revenue. Since our 2025
merger with Bigtincan, we have created the industry’s first unified platform specifically designed for complex, field-selling
organizations, serving more than 2,000 customers across 50 countries.
As an employer, we provide our employees with opportunities to grow, make a meaningful impact, and bring their authentic selves to
work. Our culture stems from our values, which center on achieving maximum impact for our customers and fostering global
collaboration, diversity, and a genuine passion for innovation. We’re a team of authentic, good-natured ass-kickers, and we’ve
been recognized as a top workplace by Built In Chicago and Inc. Magazine.
Why Join Us Now?
Showpad is powering the next generation of field selling success through accelerated innovation, expanded global reach, and a more
holistic engine to drive growth and lasting value. You’ll join a team shaping what’s next, working with smart, driven people who
care deeply about making an impact (and aren’t afraid to challenge the status quo).
Our Global Footprint
Founded in 2011, Showpad is a global company with 1,000+ people (post-merger) working from offices and regional hubs around the
world including Chicago, Boston, Ghent, London, Munich, Brussels, San Francisco, and Sydney. We are consistently recognized as a
Leader in the Forrester Wave™ and a “Customers’ Choice” by Gartner® Peer Insights.
What you can expect from Showpad
We welcome every voice and are committed to building a truly inclusive environment where your differences are not just welcomed,
they are celebrated. We’re building a best-in-class experience for our employees and are always identifying opportunities to
encourage our team to be their authentic selves. Whether that’s paid parental leave, paid holidays (including Juneteenth and paid
time off to vote), paid time off to volunteer at non-profit organizations, personal development opportunities or professional
stretch assignments, you can expect Showpad to support you.
We are committed to creating a diverse and inclusive organization and are proud to be an equal opportunity employer. All qualified
applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or
expression, sexual orientation, national origin, genetics, pregnancy, disability, age, veteran status, or other dimensions of
identity.
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