Head of Technical Success
Employer: Pinpoint
Location: This is a remote role based in the UK, with occasional in-person meetups
Working hours: Full time
Salary: Not listed
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Hi 👋 I’m Dom, VP of Engineering at Pinpoint.
We’re a high-growth HR tech company building software that helps in-house recruitment teams attract, hire, and onboard the right talent. We have a mature product, strong product–market fit, and a growing base of enterprise customers.
As the business has grown, more and more critical technical customer work has landed outside any clear owner. That work spanning delivery, integrations, data, and customer-facing enablement like career sites currently sits across multiple teams and often ends up with the CTO or VP of Engineering.
That’s where you come in. We’re establishing Technical Success as a dedicated function for the first time, and we’re hiring a Head of Technical Success to own it end to end.
From day one, you'll manage two teams (4 direct reports today), Technical Account Management and Careers Site Support, and bring them together under a single operating model. You'll own technical customer outcomes across delivery and enablement, overseeing Technical Account Management, which handles implementations, integrations, data work, and complex escalations, and Careers Site Support, which builds and maintains customer-facing career sites used by Sales and customers.
You’ll act as the primary escalation point for complex technical issues, unblock Sales and CS, protect Engineering from ad-hoc work, and turn what is currently fragmented into something predictable, scalable, and trusted.
The fine print (but a bit more exciting):This is a remote role based in the UK, with occasional in-person meetups
Our product is deep, flexible, and genuinely complex; you’ll need to understand APIs, integrations, data flows, and system constraints under the hood
While we’re PE-backed, we operate with bootstrapped discipline — you’ll be expected to scale impact through process, tooling, and prioritisation rather than just adding headcount
You’ll spend a meaningful amount of time in the weeds early on, earning credibility by doing the work alongside your team
This role will not suit someone who prefers strategy, architecture, or advisory work over hands-on delivery and operational ownership
Success in this role is measured by clear ownership of Technical Success, reduced CTO and VP Engineering involvement in day-to-day customer work, faster and more predictable onboarding, strong trust from Sales and CS, and clear visibility into quality, throughput, and team capacity.
Our values actually matter here. We hire people who reflect them in how they work, collaborate, and make decisions
About the Role
Technical Delivery & Customer Outcomes (Technical Account Management)
Oversee the Technical Account Management (TAM) function day-to-day and build the function from the ground up
Own the quality and consistency of enterprise configurations, integrations, and technical delivery
Join complex customer calls when deep technical context or escalation is required, particularly around configuration, integrations, or platform behaviour
Act as the technical counterpart to Sales, CS, Implementation, and Developer Support
Drive the move toward self-service over time by identifying repeat work and reducing Engineering dependency
Customer-facing Enablement (Careers Site Support)
Lead and manage the Careers Site Support team responsible for customer- and sales-facing career sites
Ensure career sites are delivered on time, maintained consistently, and support Sales and CS effectively
Own enablement workflows that support new deals, onboarding, and ongoing customer success
Identify opportunities to improve efficiency and operational excellence across career site work, including proposing tooling, automation, or structural changes as the function matures
Team Management
Lead and manage a small, high-output team spanning Technical Account Management and Careers Site Support
Unblock your team by setting priorities, and making decisions
Hire, onboard, and develop future team members
Define and track metrics that show quality, throughput, and efficiency
Own capacity planning and throughput — understanding where the team is at capacity and defining how (and if) it scales
Identify tooling gaps and build the case for investment where needed
About You
Meaningful experience in customer-facing technical roles such as Solutions Engineering, Technical Account Management, Implementation, or Customer Engineering
Recent and substantial experience working in a startup or early scale-up environment, comfortable building structure from scratch without the support systems of a large or highly mature organisation
Experience managing customer-facing technical teams (e.g. Technical Account Managers, Customer Engineers, Implementation or Technical Success teams), with direct accountability for delivery quality, prioritisation, and escalations
Experience working with complex, configurable B2B SaaS products and enterprise customers
Strong technical fluency around APIs, integrations, and data flows in a B2B SaaS environment — enough to diagnose issues, advise customers, and identify tooling gaps (without needing to write production code)
FAQs
What teams will I be managing, and what do they do day to day?
Technical Account Management (2 people today): owns technical delivery for enterprise customers, including configuration, integrations, complex escalations, data migrations, and ad-hoc technical requests. TAMs exist to take some technical work off the plates of CSMs and Implementation Managers and act as the first line of deep technical support.
Careers Site Support (2 people today): Front-end developers building and maintaining customer-facing career sites for Sales prospects and customers, supporting demos, onboarding, and ongoing changes. This work is critical to both winning new deals and supporting customers post-sale.
Who does this role report to, and why does it sit in Engineering?
This role reports to the VP of Engineering
Sitting in Engineering gives Technical Success the leverage needed to protect engineers from ad-hoc customer work over time and create clearer escalation paths
How hands-on is this role in the first year?
Very hands-on. You’ll be close to the work — joining customer calls when escalation or deep technical context is needed, working alongside TAMs and Careers Site Support, and getting into the details of how delivery and enablement actually happen today. This is not a strategy-only leadership role.
What will my first 30 days look like?
Your initial focus will be on understanding the product and the reality on the ground. You’ll build deep product mastery across implementations, integrations, data work, and career sites, while also getting hands-on with live customer issues, escalations, and onboarding. The goal is to develop a clear picture of what’s working, what’s broken, and where effort is being spent, and start identifying gaps in playbooks, processes, and ownership.
What should be in place by around 60 days?
By this point, core playbooks should exist for the main Technical Success workstreams and common scenarios. You’ll have defined a clear operating model across Technical Account Management and Careers Site Support, built a strong understanding of the customer base (including key enterprise accounts and risk areas), and set clearer priorities for the team with better visibility into capacity and trade-offs.
What does success look like by 90 days?
Around the 90-day mark, the function should start to feel more predictable and less reactive. Team structure will be clearly defined, with hiring underway if additional capacity is needed. You’ll have delivered early wins on at-risk or high-impact accounts, and CTO and VP Engineering involvement in day-to-day technical customer work should be noticeably reduced.
What does success look like after six months?
Technical Success is operating as a clearly owned and trusted function. There’s visibility into customer health and delivery quality that didn’t exist before, onboarding is faster and more consistent, and Sales and CS know exactly when and how to involve Technical Success. You've earned credibility with customers, the team, and leadership by being close to the work and delivering results.
Is this a revenue- or quota-carrying role?
No
This role enables expansion through adoption, readiness, and delivery quality
Success is measured on efficiency, predictability, and reduced friction — not revenue targets
How big is the team today, and will it grow?
The team is 4 people today and operating at capacity
Part of this role is defining the output model and planning how (and if) the team should scale over time
How technical do I need to be?
You don’t need to write production code
You do need to understand APIs, integrations, data flows, and SaaS architecture well enough to diagnose issues, make decisions, and identify tooling gaps
What kinds of technical work cause the most friction today?
Integrations (for example, calendar integrations)
Data migrations from other ATSs
Ad-hoc data change requests that currently require Engineering support
What We Offer
We want Pinpoint to be the best place you’ve ever worked—somewhere you feel valued, supported, and excited to grow. Here’s what you’ll get:
Comprehensive healthcare – Excellent medical, dental, & vision coverage for you and your family
Unlimited holidays – Take the time you need to rest and recharge
Mental health support – Unlimited, immediate access to professional counseling via Spill
Retirement contributions – 401k or pension contributions depending on your location
Remote-first – Work where you’re most productive, with flexibility and trust as the default
Equity with real upside – Share in the long-term value you help create
Fully paid parental leave – Up to 16 weeks of paid leave for new parents
Learning budget – Annual funds for courses, books, or anything that supports your growth
A detailed overview of our benefits can be found here.
About Pinpoint
We’re changing the way companies hire, and rewriting the rules of recruitment.
We’re a high-growth HR tech company building software that makes hiring faster, fairer, and more human, fixing the broken processes that make it hard for great candidates and great companies to find each other.
Founded in 2018, we bootstrapped our way to 500+ customers and $5M ARR before raising private equity funding in 2023 to support our next stage of growth. Today, we’re a 90-person team across the U.K. and U.S., serving more than 1,000 organizations worldwide. We scale deliberately, with sensible unit economics and no layoffs, because we’re building for the long term—not the next funding round.
Our product is deep and configurable enough to support complex hiring workflows, yet simple enough for teams to love using every day. That balance is what makes Pinpoint different. We back it up with genuine care, including fast (under 90 seconds) support from real people who know the product.
Our culture is built on genuine transparency and values we actually use to make decisions. Even as we’ve moved past early-startup noise, everyone here still shapes how we operate—taking ownership, staying curious, and solving problems proactively. As we scale, we balance structure with flexibility while holding ourselves to a high bar for respect and kindness.If you’re excited by meaningful problems, high ownership, and working with smart, kind teammates, we’d love to hear from you.
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