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Practising for the listing Senior Director, Product Management (AI/ML). Its requirements are filled in below. When you have an answer you like, paste it with your CV in Career Mirror to see which of the job's skills it shows.

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Senior Director, Product Management (AI/ML)
Attentive® is the AI marketing platform for 1:1 personalization redefining the way brands and people connect. We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships. By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and loyalty through real-time behavioral insights.

Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries. Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in revenue for our customers.

With a distributed global workforce and employee hubs in New York City, San Francisco, London, and Sydney, Attentive’s team has been consistently recognized for its performance and culture. We’re proud to be included in Deloitte’s Fast 500 (four years running!), LinkedIn’s Top Startups , Forbes’ Cloud 100 (five years running!), Inc.’s Best Workplaces , and the Human Rights Campaign Foundation's Corporate Equality Index !

About the Role

Attentive is building an industry-defining Marketing Agent: a unified, vertically integrated, autonomous system that builds on three years of advances to create a step change in performance for our customers.

This is a chance to define what an AI-first company looks like and change the trajectory of an industry. You will help decide what autonomous marketing should mean, build the product that makes it useful and trustworthy, and work with a stellar team to bring it to market to 1000’s of Attentive’s enterprise brands and leading companies in every vertical.

We are looking for a product leader with marketing, advertising, or ecommerce experience and AI/ML depth to turn our vision into a product that brands trust, use, and get measurable value from. You will own the product strategy and execution for the autonomous agent, working closely with engineering, research, design, machine learning, data science, GTM and our customers.

Unlike in other industries, an AI-native marketing solution does not need to simply create one deliverable – it needs to guide and operate a complete machine learning system that itself delivers 1:1 experiences at scale. You will oversee the building of that complete system.

You will co-own the revenue number for this product and partner closely with our CEO to make it a success.

This hybrid role is based in our New York office, with in-office collaboration Tuesday through Thursday each week.

What You’ll Accomplish

• Define the product thesis, strategy, and north-star outcomes for Attentive's autonomous Marketing Agent. Make clear what we are building, for whom, why it will win, and what we will deliberately not build.

• Work directly with customers and internal experts to understand how marketing decisions are made today, where automation can create leverage, and where the product must earn confidence before it acts.

• Turn an ambitious, ambiguous opportunity into a focused plan: customer problems, product principles, roadmap, sequencing, investment choices, and the decisions required to make progress.

• Own the end-to-end agent experience and operating loop - understanding a customer's business and goals, forming a plan, taking action, measuring results, learning, and improving

• Partner deeply with engineering and AI/ML teams on model strategy, data and feedback loops, tool use, retrieval, orchestration, evaluation, reliability, latency, cost, and the platform foundations required to make the product real at scale.

• Establish a rigorous system for evaluating the agent. Define the metrics, experiments, and failure analysis that tell us how much and why it is genuinely improving customer outcomes.

• Lead across boundaries. Clarify ownership, resolve disagreements, surface risks early, and build alignment without waiting for someone else to solve the problem for you.

Your Expertise

• 10+ years in product management or a closely related product leadership role, including substantial ownership of AI/ML-powered products. We care more about the level and quality of your experience than an exact number of years.

• A senior product leader who has shipped consequential AI/ML products and can connect technical possibility to customer value and business outcomes.

• Experience leading 0-to-1 products in a setting where the right answer was not obvious and the path changed as you learned. Experience with agents, decision systems, or applied generative AI is especially relevant.

• Enough technical fluency to engage credibly with researchers and engineers on model behavior, evaluation, data quality, system architecture, tradeoffs, and failure modes.

• Strong product judgment: the ability to identify the highest-leverage problem, make hard tradeoffs, simplify complexity, and distinguish a real product insight from a compelling story.

• A demonstrated habit of using customer evidence, experiments, and honest metrics to make decisions. You are comfortable showing that something failed when that is what the data says.

• The ability to operate as the mini-GM of a product area: set direction, create clarity, communicate directly, and take responsibility for outcomes across functions.

You'll get competitive perks and benefits , from health & wellness to equity, to help you bring your best self to work.

For US based applicants:

• The US base salary range for this full-time position is $281,600 - $352,000 annually + equity + benefits

• Our salary ranges are determined by role, level and location

#LI-HB1

By applying for this position, your data will be processed as per Attentive's Privacy Policy .
Attentive Company Values

Default to Action - Move swiftly and with purpose

Be One Unstoppable Team - Rally as each other’s champions

Champion the Customer - Our success is defined by our customers' success

Act Like an Owner - Take responsibility for Attentive’s success

Learn more about AWAKE , Attentive’s collective of employee resource groups.

If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.

At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.

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Requirements found

Marketing (must)

What this posting asks for

Level: Manager — The title says "Director".

Main responsibilities

Work directly with customers and internal experts to understand how marketing decisions are made today, where automation can create leverage, and where the p…
Own the end-to-end agent experience and operating loop - understanding a customer's business and goals, forming a plan, taking action, measuring results, lea…
Partner deeply with engineering and AI/ML teams on model strategy, data and feedback loops, tool use, retrieval, orchestration, evaluation, reliability, late…

Competencies an interviewer will look for

Technical skill Core
In the posting: “You will own the product strategy and execution for the autonomous agent, working closely with engineering, research, design, machine learning, data science,…” · “Partner deeply with engineering and AI/ML teams on model strategy, data and feedback loops, tool use, retrieval, orchestration, evaluation, reliability, late…” · “Enough technical fluency to engage credibly with researchers and engineers on model behavior, evaluation, data quality, system architecture, tradeoffs, and f…”
Show it by: Names the tools, languages or systems used and how; Explains a technical choice and its trade-off.
Ownership and accountability Core
In the posting: “Attentive is building an industry-defining Marketing Agent: a unified, vertically integrated, autonomous system that builds on three years of advances to cre…” · “You will help decide what autonomous marketing should mean, build the product that makes it useful and trustworthy, and work with a stellar team to bring it …” · “You will own the product strategy and execution for the autonomous agent, working closely with engineering, research, design, machine learning, data science,…”
Show it by: Takes a task from start to finish without being chased; Owns a mistake and what was changed after it.
Customer focus Core
In the posting: “We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships.” · “Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries.” · “Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in re…”
Show it by: Puts the customer's need in their own words; Shows a result for the customer, not only for the company.
Planning and organisation Core
In the posting: “Turn an ambitious, ambiguous opportunity into a focused plan: customer problems, product principles, roadmap, sequencing, investment choices, and the decisio…” · “Own the end-to-end agent experience and operating loop - understanding a customer's business and goals, forming a plan, taking action, measuring results, lea…” · “We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation.”
Show it by: Shows how priorities were set when everything was urgent; Mentions deadlines met and how.
Data and analysis Core
In the posting: “By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and …” · “You will own the product strategy and execution for the autonomous agent, working closely with engineering, research, design, machine learning, data science,…” · “Partner deeply with engineering and AI/ML teams on model strategy, data and feedback loops, tool use, retrieval, orchestration, evaluation, reliability, late…”
Show it by: Uses a number to describe the situation or the result; Explains what the data showed and what was done with it.
Attention to detail and quality Core
In the posting: “We care more about the level and quality of your experience than an exact number of years.” · “Enough technical fluency to engage credibly with researchers and engineers on model behavior, evaluation, data quality, system architecture, tradeoffs, and f…”
Show it by: Gives an example of an error caught before it caused harm; Names the check or standard they used.
Stakeholder management Core
In the posting: “Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries.” · “Clarify ownership, resolve disagreements, surface risks early, and build alignment without waiting for someone else to solve the problem for you.”
Show it by: Shows how they aligned people with different goals; Explains how they handled a 'no' from someone senior.
Problem solving Supporting
In the posting: “Clarify ownership, resolve disagreements, surface risks early, and build alignment without waiting for someone else to solve the problem for you.”
Show it by: Describes a real problem, the options considered and the one chosen; Shows how the cause was found, not just the fix.
Communication Supporting
In the posting: “The ability to operate as the mini-GM of a product area: set direction, create clarity, communicate directly, and take responsibility for outcomes across fun…”
Show it by: Adapts the message to the listener; Gives an example of explaining something clearly in writing or speech.
Teamwork and collaboration Supporting
In the posting: “This hybrid role is based in our New York office, with in-office collaboration Tuesday through Thursday each week.”
Show it by: Says what they did inside a team, not only what 'we' did; Shows how a disagreement was handled.
Leadership and mentoring Supporting
In the posting: “10+ years in product management or a closely related product leadership role, including substantial ownership of AI/ML-powered products.”
Show it by: Describes setting direction or a standard others followed; Names someone they coached and what changed for them.
Adaptability and learning Supporting
In the posting: “Turn an ambitious, ambiguous opportunity into a focused plan: customer problems, product principles, roadmap, sequencing, investment choices, and the decisio…”
Show it by: Describes learning something new quickly and using it; Shows a change of plan and how they adjusted.

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Practice questions

Tell me about yourself. Dedicated step-by-step practice.
If an interviewer asks something improper How to respond to questions about age, family, origin or health.
Built from this posting (8):
Walk me through a piece of work where you used your strongest technical skill. What exactly did you do? From this posting
Tell me about a task you took from start to finish without anyone asking you to. From this posting
Describe a time you went out of your way to solve a customer's problem. From this posting
You have three urgent tasks due today and time to finish only two. How do you decide? From this posting
How have you used marketing in your work? Walk me through one real example. From this posting
Tell me about a time you helped someone on your team get better at their work. From this posting
Tell me about a difficult problem you solved at work. How did you find the cause? From this posting
Tell me about a time you had to explain something complex to someone outside your field. From this posting
This posting reads as Product management: its questions come first.
Tell me about a product decision you made based on what users told you. Product management
You have ten feature requests and capacity for three. How do you choose? Product management
Describe a time you had to say no to a senior stakeholder. Product management
How do you decide whether a feature you launched worked? Product management
Tell me about a launch that involved several teams. What was your role? Product management
A key feature is late and the launch date is fixed. What do you do? Product management
How do you write requirements so that engineers and designers build the right thing? Product management
Tell me about a product failure you were responsible for. Product management
Describe a time you handled an upset customer or colleague.
Tell me about a time you had several deadlines at once. How did you decide what to do first?
Give an example of a mistake you caught before it caused a problem.
Tell me about a time you taught someone how to do something.
Describe a time you took the lead without being asked.
Tell me about a time you had to explain something complicated in simple terms.
Describe a process you improved.
Do you have any questions for us?
Why do you want to work here?
Why is there a gap in your employment? Difficult question
Why did you leave your last job? Difficult question
Why are you changing careers? Difficult question
What is your greatest weakness? Difficult question
What are your salary expectations? Difficult question
You seem overqualified for this role. Why do you want it? Difficult question
Improper-question practice: How old are you? / Do you have children? / Where are you from originally?
A customer is angry about a delay you did not cause. What do you do?
How do you keep track of many open customer requests?
Tell me about a time you could not give a customer what they wanted.
You find that the inventory count does not match the system. What do you do?
Tell me about a time a shipment or delivery went wrong.
How do you make sure safety rules are followed on a busy shift?
Two managers ask you to book the same room at the same time. What do you do?
How have you used spreadsheets in your work?
Tell me about a time you had to enter or check a lot of data accurately.
Tell me about a sale or agreement you are proud of.
A prospect says your price is too high. How do you respond?
How do you keep your pipeline organised?
Tell me about a technical problem you solved on your own.
You find a bug right before a release. What do you do?
Walk me through how you would check whether a report's numbers are right.