Implementation & Enablement Manager, Ottimate
$130-150k
NetSuite
Sage
Senior and Expert level
Remote from US
Accounts payable automation
Be an early applicant
Accounts payable automation
201-500 employees
HospitalityB2BArtificial IntelligencePaymentsSaaSAccountingAutomation
Be an early applicant
$130-150k
NetSuite
Sage
Senior and Expert level
Remote from US
201-500 employees
HospitalityB2BArtificial IntelligencePaymentsSaaSAccountingAutomation
Company mission
To make life a little easier for anyone eager to spend less time on AP and more time growing their business.
Role
Who you are
- 7+ years in SaaS implementation, professional services, or customer onboarding - with at least 3-4 years in a people management or formal team lead role
- Demonstrated track record of building or meaningfully improving an implementation practice - not just inheriting and maintaining one
- Experience with AP, procurement, or financial operations workflows strongly preferred; ERP or accounting system implementation experience (Sage Intacct, NetSuite, Acumatica, Microsoft BC) is a plus
- Change management experience - both leading customers through operational change and leading internal teams through process transformation
- Outcome-oriented mindset - you define implementation success by what the customer achieves, and you hold the team to that standard, not to project closure dates
- Exceptional coaching instinct - you develop people through direct feedback, observation, and example; you make the team better as a natural byproduct of how you lead
- Consultative approach - to customers and to the team; you ask the right questions before jumping to solutions, and you teach others to do the same
- Strategic thinker who can also execute - you can hold the vision for where implementation should go while staying close enough to the work to lead through the day-to-day
- Direct and clear communicator - comfortable delivering hard feedback to your team, navigating difficult customer conversations, and representing the team in cross-functional settings
- Comfortable with ambiguity and organizational transformation - this function is evolving, and you'll be shaping it as much as running it
What the job involves
- As Manager, Implementation & Enablement, you will lead the team responsible for bringing Ottimate customers from signed contract to realized value
- This is a hands-on leadership role: you will be close enough to the work to coach through it, evolve the process around it, and remove the barriers that slow your team down - while staying accountable for the outcomes the team delivers at scale
- This role is not about managing timelines
- It's about managing outcomes
- You will define what a successful implementation looks like at Ottimate, build the methodology that gets customers there consistently, and hold your team to a standard where implementation is complete when the customer achieves value, not when the project closes
- You will work cross-functionally with Sales, Customer Success, and Product & Engineering, serving as the connective tissue between what customers were promised and what they experience
- As Ottimate grows, this role grows with it - from operational leader to a key voice in how the broader Services organization evolves
- Lead, develop, and retain a team of Implementation Managers and Enablement Consultants - building a culture of accountability, continuous improvement, and customer focus
- Coach team members through live engagement feedback, structured 1:1s, and deliberate skill-building - developing and growing talent, not just managing performance
- Establish clear expectations, performance standards, and growth paths for every person on the team
- Elevate the people around you: your success metric is not just what you deliver, but how much better the team gets under your leadership
- Model the behaviors - ownership, consultative instinct, reliability, product depth - that define excellence in this function
- Own and evolve Ottimate's implementation methodology, building an outcome-driven delivery model where customer-centric milestones - not arbitrary project timelines - define value
- Translate customer goals into a structured, measurable implementation experience that creates a repeatable path to value across different customer profiles and system configurations
- Build and maintain implementation playbooks, frameworks, and escalation guides that raise baseline delivery quality and make the team faster and more efficient as it scales
- Serve as an escalation point for delivery risk and complex client issues - stepping in when the team needs senior judgment, not just process support
- Ensure documentation standards are upheld across all active engagements; implementation knowledge should live in the system, not with individuals
- Bring a consultative approach to customer engagements - helping customers navigate the organizational change that comes with adopting new AP workflows, not just configuring software
- Partner with customers at the leadership level when needed, translating Ottimate's implementation model into their language and building confidence in the process
- Lead through ambiguity: implementations rarely go as planned, and this role requires someone who can adapt and keep both the customer and internal teams aligned
- Identify patterns where implementations stall and proactively address the root causes rather than managing symptoms
- Partner closely with the Solution Architect to ensure clean transitions between pre-sales scoping and implementation execution
- Collaborate with Customer Success on account health, escalations, and the move from implementation to long-term customer ownership
- Work with Product & Engineering on JIRA ticket prioritization, custom configuration needs, and product gaps that surface repeatedly during implementation
- Partner with Sales to align on customer expectations before contracts are signed - not after - so implementation begins with shared, realistic goals
- Represent the implementation function in cross-functional leadership conversations, contributing the delivery perspective to process, tooling, and roadmap decisions
- Own implementation team capacity planning, resource allocation, and workload management across the portfolio of active engagements
- Define and track the metrics that matter: time-to-live, utilization rates, customer satisfaction at go-live, and team delivery consistency
- Contribute to the broader Services org strategy - this role is not just about running implementations well today, but helping shape what the function looks like as Ottimate scales
Our take
Accounts payable is a cumbersome side of financial management for the hospitality and restaurant sectors. High volumes of deliveries, along with the chance of damage to perishable items, means that keeping track of short-term credit to various sellers is a tricky business.
Ottimate's solution is to effect digital transformation across B2B payments and accounts payable in the hospitality sector. The company’s VendorPay allows customers to make payments directly to over 200,000 vendors straight from their AP platform, streamlining and resolving the late payments issue that’s been growing steadily in the sector.
Margins in the sector are famously tight, so even the most modest of operational improvements can make substantial gains for hospitality businesses. Indeed, over 30,000 restaurants, hotels and grocery chains across the US are using Ottimate’s platform, including leading brands such as Best Western, Holiday Inn and Foodtown.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Top investors
29% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Nov 2021
$160m
SERIES B
Mar 2017
$4m
SERIES A
Total funding: $164.7m
Company benefits
- Health & Retirement: We offer comprehensive medical, dental, vision coverage as well as a 401(k)
- Paid Time Off: We offer plenty of vacation and personal time off to give you the time to step away, unwind, and recharge
Company HQ
SoMa, San Francisco, CA
Leadership
Barrett Boston
(CEO)Previously CRO and Executive Officer for TriNet. Before that, they were the President of Americas with TravelClick and Vice President at IBM.
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