Lone Wolf Technologies

Lone Wolf Technologies

Real estate transaction and back-office software

Customer Success Operations Analyst - Gainsight

Full-Time
CA$105k/yr
Mid
Toronto, ON, Canada
Remote

About the job

Requirements
  • At least 3 years of hands-on Gainsight administration experience in a production environment.
  • Demonstrated experience building a Gainsight implementation rather than using Gainsight only as an end user.
  • Deep hands-on experience with Journey Orchestrator, including building multi-step automated journeys, participant logic, and triggers.
  • Strong experience with Rules Engine, Customer Health and Scorecards, Playbooks, Success Plans, Reports, and Dashboards.
  • Experience working with Salesforce and understanding CRM data models, account structures, and integrations.
  • Experience translating business requirements into scalable technical configurations.
  • Strong troubleshooting, analytical, and data-management skills.
  • Strong understanding of Customer Success workflows including onboarding, adoption, risk management, retention, and lifecycle engagement.
Responsibilities
  • Serve as the primary administrator and technical owner of Gainsight CS.
  • Configure and maintain Gainsight objects, fields, layouts, permissions, health scores, CTAs, playbooks, Success Plans, reports, dashboards, and automation.
  • Build and manage Journey Orchestrator programs, including audience criteria, branching logic, triggers, and automated communications.
  • Partner with Customer Success leadership to translate customer journey and lifecycle strategies into scalable Gainsight workflows.
  • Build and maintain Rules Engine configurations, data transformations, reporting logic, and automated customer health and risk signals.
  • Partner with other system owners to integrate and operationalize customer data within Gainsight.
  • Support the integration and use of Gainsight PX and Skilljar as part of broader digital adoption and customer education motions.
  • Establish platform governance, documentation, testing, change management, and administration standards.
  • Train and enable Customer Success users while continuously improving workflows and reducing administrative friction.
Desired Qualifications
  • Gainsight Administrator certification or equivalent demonstrated expertise.
  • Experience with Gainsight PX and Skilljar.
  • Experience in a multi-product SaaS environment.
  • Familiarity with SaaS metrics including ARR, GRR, NRR, churn, contraction, and product adoption.

About the company

Lone Wolf Technologies

Lone Wolf Technologies

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At Lone Wolf Technologies, we believe making tech for real estate is about much more than just making the best tools. It’s about making them connect, all in one place—to make real estate simple. Our mission is to provide agents, brokers, admins, and associations alike with the technology tools they need to lead in real estate—from the leading transaction solutions in North America to the industry standard in back office and accounting. We’ve been in real estate since our very first day, over 30 years ago now—and in that time, we’ve worked with our users to create technology that works the way they do, connects the way they do, and provides an exceptional experience the way they do.

Company Size

501-1,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Cambridge, Canada

Founded

1989

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Simplify Jobs

Simplify's Take

What believers are saying

  • July 2026 Talent and Aspen launches deepen AI inside existing broker workflows.
  • February 2026 API Portal expands integrations and reduces data silos for customers.
  • More than 1.5 million professionals and 10,000 brokerages provide cross-sell leverage.

What critics are saying

  • Talent’s fall 2026 launch misses if Aspen underdelivers beyond BrokerMetrics preview.
  • No layoffs or litigation surfaced, but integration complexity can stall customer adoption quickly.
  • Real estate software consolidation threatens Lone Wolf’s point-solution margins if brokers switch to bundled rivals.

What makes Lone Wolf Technologies unique

  • Foundation centralizes transactions, accounting, CRM, and MLS data across workflows.
  • BrokerMetrics uses licensed nightly MLS data across 10,000 brokerages for recruiting intelligence.
  • Matt Fischer brought Bullhorn scaling discipline and completed the 2026 leadership overhaul.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Health Insurance

401(k) Retirement Plan

Remote Work Options

Paid Vacation

Flexible Work Hours

Conference Attendance Budget

Professional Development Budget

Wellness Program

Mental Health Support

Stock Options

Company Equity

Phone/Internet Stipend

Home Office Stipend

Family Planning Benefits

Fertility Treatment Support

Adoption Assistance

Childcare Support

Parental Leave

Pet Insurance

Bereavement Leave

Holidays

Profit Sharing

Growth & Insights and Company News

Headcount

6 month growth

↑ 10%

1 year growth

↑ 10%

2 year growth

↑ 12%
Real Estate News
Sep 22nd, 2026
Former Lone Wolf GM joins MAVERIX as strategic advisor.

Former Lone Wolf GM joins MAVERIX as strategic advisor. Kyle Hunter moves to the consultancy after 15+ years at Lone Wolf. Plus, Florida-based Coldwell Banker Anabasis Realty names Shaun Guerard president of sales. September 22, 2026 Editor's note: As an industry with millions of agents and over 100,000 brokerage companies, new leaders rise to the top every day. Here we highlight executives and other notable leaders who've recently taken on, or stepped away from, roles that influence the residential real estate landscape. Lone Wolf exec moves to MAVERIX. MAVERIX announced today that it has appointed Kyle Hunter to serve as a strategic advisor, adding an executive with nearly three decades of experience in real estate technology, operations, sales and strategic partnerships to the firm. Hunter previously held several senior leadership roles at Lone Wolf Technologies, including general manager of franchise and industry principal, working with real estate brands and brokerage organizations across North America. As a strategic advisor at MAVERIX, Hunter will partner with the company's leadership and advisory team on client engagements involving growth, go-to-market strategy, enterprise relationships and changes in the real estate tech sector, according to a news release. MAVERIX Founder and CEO Jeff Kennedy praised Hunter's decades of experience and sterling reputation in the industry, adding that he is "the type of person we want to partner with" at MAVERIX. "He also happens to be a good human being with a great reputation in our industry, and someone that people genuinely like and trust. That matters to me. A lot," Kennedy wrote in a post on LinkedIn. "Kyle checks every box. And he's fully bought in to the MAVERIX mission." Florida CB affiliate adds president of sales to bolster growth. Coldwell Banker Anabasis Realty, a Coldwell Banker affiliate based in Macclenny, Florida, has tapped Shaun Guerard to serve as president of sales. In his new role, Guerard will focus on recruiting, agent development and continued expansion across Northeast Florida and South Georgia. Guerard brings over 20 years of real estate leadership experience and has coached and developed more than 250 real estate professionals, according to a news release. His background includes leading sales teams, developing agent organizations and implementing systems aimed at boosting productivity, transaction volume and market share - and he has already contributed to growth at the brokerage's offices in Macclenny and Valdosta, Georgia, the firm said. Co-owner Bryce Ocepek said the appointment is a milestone for the brokerage as it works to improve agent performance and expand its market position. Meanwhile, Guerard described his approach as being centered on creating an environment where agents can thrive, with a strong workplace roster serving as the foundation for long-term business success. Editor's note: AI was used in the initial drafting of this content, which was then thoroughly reviewed, fact-checked and revised by a Real Estate News editor.

Inman
Aug 20th, 2026
MoxiWorks taps Shaun Harkley as new SVP of Sales.

MoxiWorks taps Shaun Harkley as new SVP of Sales. Harkley's hire marks the 3rd executive addition at MoxiWorks in recent months Today, August 20, 2026 MoxiWorks has named Shaun Harkley its new senior vice president of sales, effective Sept. 14, bringing in a sales leader from rival proptech firm Rechat to lead the company's global sales organization. Harkley will oversee MoxiWorks' sales teams across North America, Australia, New Zealand and the U.K., reporting directly to CEO Eric Elfman and sitting on the company's executive leadership team, the company announced Wednesday. His mandate is to build on the company's existing sales base and push RISE - MoxiWorks' AI-native product - into more brokerages worldwide. Harkley joins from Rechat, where he served as head of sales, and previously held sales roles at Lone Wolf Technologies. Earlier in his career, he worked in global sales leadership at Resolver, a risk intelligence software company outside real estate. He was named a HousingWire 2026 Rising Star earlier this year. "Shaun is exactly the kind of leader we need for this next chapter at MoxiWorks," said Eric Elfman, CEO of MoxiWorks, in a statement. "He has spent his career building winning sales organizations in this industry, and he knows what it takes to help brokerages and agents grow. We're thrilled to have him lead our global sales team as we expand RISE." Harkley's move from Rechat - a competitor in the brokerage tech space - is notable on its own. The pull may have been less about leaving Rechat and more about where MoxiWorks is headed, however. "I chose MoxiWorks because it brings together everything I was looking for in my next opportunity: an incredible team, products I genuinely believe in and a massive opportunity for growth," said Harkley. "Having competed in this space, I've seen firsthand how products like ActivePipe and MoxiPresent have become best in class, and the momentum behind RISE makes what's ahead even more exciting." The hire is the third executive addition at MoxiWorks in recent months, following Chief Product Officer Ashley Fidler, PhD, and Chief Marketing Officer Kim Koraca. It's a buildout that suggests MoxiWorks is staffing up its C-suite ahead of a broader RISE rollout rather than making a single opportunistic hire. MoxiWorks says it now serves more than 3,000 brokerages and 400,000 agents globally.

Associated Press
Jul 28th, 2026
Lone Wolf unveils AI-powered agent recruiting tool for real estate brokerages

Lone Wolf Technologies has unveiled Talent in BrokerMetrics, an AI-powered solution for agent recruiting and retention, set for general release in autumn 2026. The platform addresses a critical gap: whilst a 2026 Inman and Lone Wolf survey found brokerages rate retention value at 8.17 out of 10, only 2% treat it as a deliberate strategy and 44% track no flight-risk signals. Talent introduces Aspen, Lone Wolf's AI assistant, which performs five functions: identifying recruitment prospects, building recruitment pitches, flagging retention risks, answering queries in plain English, and surfacing agents' social media activity. The solution uses licensed MLS data refreshed nightly, currently serving more than 10,000 brokerages. Lone Wolf serves over 1.5 million real estate professionals across North America.

HousingWire
Jul 28th, 2026
Lone Wolf bets future of real estate AI is embedded, not standalone.

Lone Wolf bets future of real estate AI is embedded, not standalone. Lone Wolf Technologies CEO Matt Fischer detailed the product launch in an exclusive interview Article Summary. Lone Wolf Technologies has launched Talent, an AI-powered module for its BrokerMetrics analytics platform, and Aspen, an AI teammate designed to work across its software ecosystem. Talent helps brokers recruit and retain agents, while Aspen will eventually expand into transaction management and marketing. CEO Matt Fischer emphasized embedding AI into existing workflows rather than creating standalone tools. AI Summary Lone Wolf Technologies is betting that the next evolution of artificial intelligence (AI) in real estate isn't another standalone tool - it's software that quietly works alongside agents and brokers inside the platforms they already use. "I've talked to so many customers and they share the same sentiment, which is there's a lot of proliferation in their tech stacks today," CEO Matt Fischer told HousingWire. "They have to cobble a whole bunch of different point solutions together to get something end to end. And it would be much better, of course, if the platforms were capable of doing all of that in a single spot." Today, Lone Wolf announced Talent, a new AI-powered module for its BrokerMetrics analytics platform, and Aspen, an AI teammate designed to work across Lone Wolf's entire software ecosystem.The announcement comes months after Fischer took over as CEO, positioning the launch as an early milestone in his vision for the company's AI strategy. Talent is only in preview stage right now and will be launched in the fall. Rather than introducing AI as a separate product, Lone Wolf is embedding it into existing workflows - beginning with Talent and expanding across its broader platform in the months and years ahead. $33.25 /mo bill annually * Unlimited access to HousingWire.com * Exclusive research and housing market data * Subscriber-only newsletters and early access Read one free article now

RISMedia
Jul 28th, 2026
Lone Wolf launches ai-powered solutions for agent recruiting and retention.

Lone Wolf launches ai-powered solutions for agent recruiting and retention. Named 'Talent,' the first release of the next phase of its AI roadmap, introduces "Aspen," Lone Wolf's AI teammate, which will help brokers recruit and retain agents by using data to create a clear picture of agent production, movement and market share. Reading Time: 2 mins read Lone Wolf Technologies has announced the release of the next phase of its AI roadmap for BrokerMetrics(R), the company's brokerage analytics and market intelligence platform that aims to help brokers recruit and retain agents. Named 'Talent,' the first release is part of a broader roadmap and introduces "Aspen," Lone Wolf's AI teammate, which will be generally available in fall 2026. According to a 2026 survey by Lone Wolf, brokerages rated the value of retaining an agent at 8.17 out of 10, well above the value they placed on recruiting a new one. Only about 2% treat retention as a deliberate strategy. Talent aims to close that gap using the data brokerages already trust. BrokerMetrics runs on licensed MLS data refreshed nightly and is used by more than 10,000 brokerages, giving brokers a clear picture of production, movement and market share, according to Lone Wolf. "We're investing in AI and the future of BrokerMetrics," said Matt Fischer, CEO at Lone Wolf. "Our data has always been among the best in the industry. Now it's much easier to act on, and this is just the beginning." Aspen will handle jobs including: * Recruit: Identifies agents whose production and movement patterns fit a brokerage's growth goals. * Pitch: Builds the case for why a specific agent should make the move. * Retain: Flags flight-risk signals while there is still time to have the conversation. * Answer: Fields questions in plain English, so brokers can ask what they want to know instead of building a report to find out. * Social Research: Surfaces an agent's public social activity in a single click * Mapping: Allows brokers to draw a recruiting territory on a map and see the agent opportunity inside it.