Director, Sales Enablement & Effectiveness

Viventium Software•,

About The Position

The primary purpose of the Director, Sales Enablement & Effectiveness role is to improve sales performance by increasing win rates, especially on larger and more strategic deals, as Viventium and Apploi move upmarket into mid-market and enterprise sales. The role is responsible for identifying why larger opportunities do not convert at the rate or size they should, and then building the enablement programs, coaching structures, sales methodology, and training needed to fix those gaps. This role directly supports the organization’s growth strategy by helping the combined Viventium/Apploi business close bigger deals more effectively, improve average deal size, and strengthen execution across the commercial organization. It serves as a critical link between sales strategy and field execution, ensuring that sales leaders, reps, Solutions Consultants, and partnership teams have the tools, knowledge, messaging, and coaching needed to succeed in a more complex enterprise selling environment. In short, the role helps translate the company’s upmarket growth goals into repeatable commercial performance.

Requirements

7+ years in sales enablement, sales effectiveness, sales, or related GTM operations roles at B2B SaaS companies
Direct experience scaling enablement at a B2B SaaS company moving from a high-velocity SMB sales motion (sub-30-day cycles, sub-$25K ACV) into a mid-market or enterprise motion (4–9 month cycles, $50–500K ACV); healthcare, HCM, payroll, RCM, post-acute, or vertical SaaS preferred
Demonstrated experience standing up win/loss programs, coaching cadences, and deal inspection rituals
Experience designing multi-track enablement curriculum across multiple knowledge axes — product, domain, and vertical — with role-based tracks for AEs, Solutions Consultants, and managers
Hands-on experience with HubSpot CRM and Salesforce
Hands-on with Gong or comparable conversation intelligence platforms; track record of expanding adoption among managers and reps
Methodology fluency across multiple frameworks (e.g., MEDDPICC, MEDDIC, SPICED, Challenger, Force Management Command of the Message, Sandler, Miller Heiman) with the ability to recommend a fit-for-purpose approach and a credible adoption plan
Strong analytical fluency — comfortable with raw data, with the rigor to validate before drawing conclusions
Track record of partnering with sales leaders to extend their effectiveness rather than substitute for it
Excellent cross-functional collaboration and stakeholder management skills
Strong facilitation and communication skills; comfortable presenting to sales leaders and large groups

Nice To Haves

Healthcare or healthcare-adjacent SaaS background (e.g., Phreesia, PointClickCare, MatrixCare, athenahealth, Tebra, Veeva, R1, Waystar, or comparable)
HCM, payroll, or workforce management background (e.g., Paylocity, Paycor, Paychex, Dayforce, ADP, UKG, Rippling, Gusto)
Solutions Consulting or sales engineering enablement experience
Channel and partnership enablement experience
LMS rollout experience (Docebo or comparable)
AI-augmented enablement tooling experience (Gong AI Trainer, Demodesk, Oliv, Weflow, etc.)
PE-backed company experience
Experience supporting a post-merger commercial integration

Responsibilities

Build a clear understanding of the Viventium and Apploi commercial organization, including segment structure, current sales process, manager cadence, tech stack, and major performance gaps.
Complete listening sessions with key stakeholders across Sales, Solutions Consulting, Partnerships, Marketing, Product, and RevOps.
Review current pipeline data, win/loss trends, Gong usage, onboarding materials, existing enablement content, and partnership messaging.
Identify the most immediate breakdowns affecting large-deal conversion, coaching consistency, and knowledge transfer.
Deliver an initial assessment of priority opportunities, risks, and recommended focus areas.
Launch a formal win/loss analysis program and present first-round findings to commercial leadership.
Rebuild and align coaching cadences with each segment leader, including weekly pipeline reviews, biweekly skill coaching, and monthly business reviews.
Stand up a deal inspection program for deals ≥$50K, including scorecards, review cadence, and clear ownership.
Evaluate and recommend the right sales methodology (or combination of methodologies) for both the high-velocity and upmarket motions.
Establish credibility as a trusted partner to sales leaders, managers, and cross-functional stakeholders.
Roll out the selected sales methodology with manager enablement, reinforcement plans, and integration into deal reviews, CRM workflows, and coaching.
Launch role-based curriculum for AEs, Solutions Consultants, and managers across product, domain, and healthcare segment knowledge.
Implement structured onboarding and certification paths that improve ramp clarity and reduce time to productivity for new hires.
Increase adoption and consistency of Gong-based coaching workflows across managers and reps.
Deliver measurable improvements in enablement discipline, knowledge consistency, and inspection rigor across the commercial organization.
Drive measurable improvement in win rates on deals ≥$50K, along with growth in enterprise and large-deal closed-won count and dollar value.
Improve average deal size by helping the organization convert larger opportunities closer to their entry value.
Establish a durable enablement operating system spanning onboarding, ongoing training, manager coaching, deal inspection, methodology, and knowledge management.
Fully deploy and operationalize Docebo (or equivalent LMS discipline) as a maintained source of truth for commercial learning and readiness.
Strengthen consistency of value messaging, competitive positioning, partnership fluency, and field execution across the combined Viventium / Apploi organization.
Play a meaningful role in supporting commercial integration readiness ahead of the January 2027 combined go-live.
Become a core driver of commercial effectiveness and an embedded partner to leadership in scaling the combined business upmarket.
Help create a repeatable model for onboarding, manager coaching, methodology adoption, and large-deal execution that can scale with organizational growth.
Contribute materially to improved sales productivity, stronger manager effectiveness, and lower first-year attrition through better ramp, clearer expectations, and stronger role readiness.
Identify why larger and more strategic deals are not converting at the rate or value they should, and turn those insights into practical enablement programs that improve win rates.
Build and run core sales effectiveness programs, including win/loss analysis, deal inspection, manager coaching cadences, and methodology adoption.
Design and deliver onboarding, training, and role-based curriculum for Account Executives, Solutions Consultants, and sales managers.
Partner closely with Sales Leadership to improve coaching consistency, increase Gong adoption, and strengthen inspection rigor across the commercial organization.
Help the field sell more effectively by improving value messaging, competitive positioning, partnership fluency, and readiness for new product, pricing, and go-to-market changes.
Create and maintain a more disciplined enablement infrastructure, including documented curriculum, certification paths, knowledge management, and effective use of the sales tech stack.
Work cross-functionally with Sales, Marketing, Product, RevOps, Implementation, and Partnerships to ensure enablement reflects the reality of the business and supports commercial performance as Viventium and Apploi continue moving upmarket.