4 Tips for Launching a 30-60-90 Day Enablement Program for Your New Sales Hires

4 Tips for Launching a 30-60-90 Day Enablement Program for Your New Sales Hires

Olivia Ramirez 18 min
By Olivia Ramirez

Without a 30-60-90 day enablement plan for your newest cohort of sales hires, you’re relying on your team to find the answers, request extra one-to-one time with their manager and peers, and hope they hit their goals. 

When you have a team in the double or triple digits and managers with their own set of favorite plays and individual workstyles, it’s all about luck. The sales development representatives (SDRs) and account executives (AEs) who pride themselves on self-reliant problem-solving will thrive, while the rest will struggle to hit their quotas for generating qualified meetings or revenue.

A 30-60-90 day enablement program will help more of your SDRs and AEs rise to the top — regardless of their learning styles and who their managers are. It’s a win-win for your sales team and your company. 

Patryk Odedina, Director of Sales Enablement at Metropolis, says that after launching the first 30-60-90 day enablement programs at his previous companies, Better and Sharebite, a high percentage of new sales hires became top performers in their first month in their new role. For example: After an SDR at Sharebite completed their enablement training, they booked more qualified meetings than Sharebite’s seasoned SDRs.

“Without enablement, the people who are innately better at sales are going to rise to the top, but you’re going to lose a lot of people from the bottom who can’t self-educate,” says Patryk Odedina, Director of Sales Enablement at Metropolis. “With enablement, the top performer may be the same, but you’re going to capture the people who wouldn’t have been able to self-educate. Instead of losing five, maybe you’ll lose two [new hires].”

He adds, “The people who have enablement are going to perform better every time [compared to those who don’t].”

If you’re launching your company’s first sales enablement program, that’s great news. You’re about to open a door to huge growth potential for your sales team. We compiled five tips to help you navigate where to focus your efforts for the best 30-60-90 day enablement results. 

What to expect: 

Tip #1: Map Your Curriculum to Your Sales Team’s Goals

Bake your sales team’s goals and their wants into the curriculum for your 30-60-90 day enablement program. 

“Your sales team is your client,” says Odedina. “It doesn’t matter if you have the best data or the best intentions; You need to ensure they are satisfied.”

The goals of individuals on your sales team might include: 

  • Conducting a minimum number of outbound emails and cold calls each week
  • Generating a minimum number of responses from their outbound sequences
  • Qualifying a minimum number of inbound leads
  • Generating a minimum number of qualified meetings
  • Becoming adept at objection handling and knowing talking points regarding your software versus your competitors’
  • Knowing how to use your internal revenue stack to complete their daily responsibilities efficiently (Not understanding how to use LinkedIn Navigator or Outreach.io, for example, might hinder your sales rep’s ability to prospect).
  • Achieving a particular close-won rate
  • Maintaining a minimum amount of revenue in active pipeline
  • Hitting their quarterly revenue quota

The department-wide goals of your sales team might include: 

  • Increasing annual recurring revenue (ARR) 
  • Increasing upsells and account expansions 
  • Boosting conversion rates and shortening sales cycles
  • Boosting the average contract value (ACV)
  • Increasing the amount of revenue in active pipeline

To learn about your sales team’s goals, their existing roadblocks, and potential gaps in resources, you should: 

  • Meet with leaders from the sales team to learn about their quarterly objectives and key results (OKRs), their key performance indicators (KPIs), their team’s historic ability to hit their goals, and their optimism around hitting their quarterly and annual targets 
  • Host one-to-one meetings with individual SDRs and AEs to understand their existing roadblocks and which resources they believe are missing from their sales conversations (e.g. if your AEs would benefit from an integration one-pager with your strategic partner for co-selling
  • Sit in on your sales team’s pipeline review meetings to get a deeper look into your sales team’s challenges breaking into individual accounts or advancing opportunities
  • Become familiar with the nuances of how your sales team defines internal sales roles (Does the CSM manage upsell opportunities or does the AE?) and accounts in their pipeline (e.g. mid-market vs. commercial deals)
  • Learn about your sales team’s tech stack and how they communicate with prospects (e.g. sending video recordings via Vidyard and email sequences via Outreach). Is there an opportunity to onboard a new piece of software or integration that will help improve your sales team’s workflows and their ability to hit their goals?
  • Learn how your sales team is currently working with tech partners and channel partners to advance opportunities in their pipeline and how they could improve their co-selling process. For example: Do your AEs close more opportunities when a channel partner includes your product in a request for proposal for a mutual opportunity? Can they engage channel partners earlier in the sales cycle to shorten the sales cycle?

Include all of the above learnings in your enablement curriculum to help your new SDRs and AEs get up to speed. Your sales enablement curriculum should include education about: 

  • Your product and features, including providing resources like one-pagers and documentation your customers often request 
  • Your internal sales tech stack, including how to leverage tools, plugins, and integrations for prospecting and closing opportunities 
  • Your tech ecosystem, including the integrations most relevant to their prospects (think: integrations that contribute the most to conversions and retention), which partners to reach out to and how (like Gorgias does), where prospects can find documentation on your application programming interface (API) and integration features, and various integration use cases and customer case studies
  • Who your sales team should pull in internally to help with various scenarios, like bringing in your customer support team for technical issues or your partnerships team for integration requests 

A message in Slack that informs Gorgias’s sales team how to engage partners for co-selling 

Use a variety of formats to ensure the enablement sessions and resources resonate with different learning styles among your sales team. Craft the above subject matter into any of the below formats:

  • Live enablement sessions using a presentation deck in a room or on Zoom (Tip: Put the recordings in your sales conversation recording tools like Gong and your knowledge base software like Guru
  • Role play scenarios where your new hires assume the roles of buyers and sellers during your enablement sessions or during sales team meetings 
  • Announcements and session recaps in your team communication tools like Slack, linking to relevant resources and pinned to the channel when necessary
  • Resources like sales battlecards, including example sales conversation responses and information about your competitors’ strengths and weaknesses
  • A sales playbook, or manual, that includes best practices and proven tactics for your sales team to reference and replicate, buyer profiles, and marketing resources like blog content and e-books your sales team can use in their outreach and sales conversations

A battlecard template courtesy of HubSpot

Odedina suggests providing your sales team with what they want rather than promoting a solution for a problem they don’t know they have. For example: If you have data telling you to develop enablement training for prospecting, but your sales team is requesting that you focus on training your team in presenting demos, prioritize the latter. Help your AEs improve their communication skills and conversion rates for demos, and identify opportunities for them to improve their sales decks. 

Solve a pain point that your sales team has right now, and build the foundational success that will help you get buy-in for additional training later on. Over time, work with your analytics or growth team to ensure you have the data to back up your case for investing in additional training.

Tip #2: Include Interactive Activities to Reinforce Lessons 

Sales enablement will look different depending on the size and priorities of your company. Odedina says that he’s developed enablement programs for cohorts of 200-250 sales reps and for cohorts of as little as two to three. For cohorts of any size, it’s critical to know how to keep your “students” engaged.

Odedina suggests making your enablement sessions interactive and encouraging conversation among your participants. The interactive component can include: 

  • Breakout rooms for participants to discuss what they learned and put their learnings into practice for hypothetical scenarios or to work through existing scenarios together 
  • An open discussion in your Zoom chat, where you consistently check the chat and answer questions live, or hosting the discussion live at designated points during your presentation
  • Ask one individual participants to read the slides, rather than yourself 
  • Use annotation tools to write on your Zoom screen, draw visuals, and present polls 
  • Give your participants simple quizzes during or after your sessions to reinforce what you’ve taught. Try asking questions in the Zoom chat, in Slack via polls, or through quiz makers like Intercom

Intercom’s quiz maker

Tip #3: Teach Your Sales Team to be Tech Stack Experts

The best SDRs craft thoughtful messaging relevant to their prospects’ existing needs and tech stacks. The best AEs are consultative and help guide their opportunities in implementing effective features and business practices. To do both, your sales team should leverage your partners, integrations, and tech stack insights

Sales teams are using partner ecosystem platforms (PEP) like Crossbeam to understand which tools their prospects have in their tech stacks. The partnerships or sales leader in your organization can map your prospects or opportunities to your partners’ customers to understand which accounts in your pipeline are currently customers of your partners. 

The account mapping matrix in Crossbeam showing where your sales team should invest their efforts with partners 

Then, sales teams use Sales Edge, a network-based co-selling solution from Crossbeam, to identify the most influential partners for a particular deal. Sales Edge puts the data in the tools SDRs and AEs use every day — like LinkedIn, Salesforce, and their email — so they can reach out to partners in real time for warm intros, intel about an account, or support closing a deal.

The Sales Edge Chrome Extension for prospecting on LinkedIn enables SDRs to reach out to partners for a warm intro into a prospect account.

Email alerts from Sales Edge inform your SDRs which partners can help them break into their prospect accounts and inform your AEs which partners can help them close a deal. 

Co-selling with partners helps sales teams improve their close rates, shorten sales cycles, close bigger deals, and grow their accounts through upsells and expansions. Educate your sales team about the value of partners, how to work with them, and the best tactics for co-selling, and you’ll see upticks in sales metrics across the board.

For example: 

Ometria’s SDR was struggling to break into an account until they learned that their prospect account was a new customer of their partner. Their partner’s onboarding customer success manager (CSM) offered to include Ometria as a recommended tool/integration during their customer’s kickoff meeting and put in a good word for them. This helped the SDR break into the account.

Sendoso made partner data available to their sales team at the account level in Salesforce and doubled their partner-influenced pipeline in just three months. If an opportunity is a customer of a partner, their AEs will reach out to their internal partnerships team for an intro to their partner to help accelerate the deal. If their prospect is a customer of a partner, the partnership team gets information about the partner’s relationship to the account and helps facilitate a warm intro for the SDR.

Viewing partner data in Slack

Census’s sales team identifies which of their prospects are customers of their partners for prospecting. They then reach out to their partners to gather intel about their prospect account (like what their procurement process is like and how they navigated pricing negotiations). Then, they approach their conversations with prospects using information relevant to their partner’s product. An example email to a prospect from one of Census’s SDRs:

Hey Jane,

Noticed from Linkedin that you lead data engineering for ACME Corporation, and it looks like the product team there is on Holver — I’m reaching out from the Census team, who is a Holver partner.

Are there user and company attributes living in the data warehouse that teams want in Holver to do deeper analysis? 

For example, if a ‘power user’ is defined in the warehouse and synced to enrich the user profile in Holver, Product and Marketing can now understand how conversion funnels differ between power and non-power users.

Census is a reverse ETL tool that syncs your data warehouse with Holver and other business applications, without requiring engineering code.

Here’s a short clip on how – would love to hear your thoughts.


Census’ SDR Name

Aaron Geller, previously the GTM Lead at Digital Ocean, says his sales rep increased the deal size for an account by selling a joint solution with two partners. When they observed a risk signaling they might lose the account, they brought in partners to help demonstrate the big-picture value of their joint solution. Rather than losing the deal, they increased the deal size.

Aaron Huish, previously Senior Sales Manager at Spirable, observed that his prospect was about to commit to a competitor’s product. He immediately brought in an agency partner to help educate the prospect on the value of his product. The agency flipped the scenario so that the prospect no longer considered the competitor’s product and only included Huish’s product in their request for proposal (RFP). 

Note: Work with your partnerships team to roll out co-selling motions with new tech or channel partners in waves. It can be the most difficult to implement new types of sales tactics among your SDRs since they’re likely the most junior roles in your sales org. Work with your AEs to close opportunities with your tech partners to start; Then, educate your SDRs using their wins. Learn more in our step-by-step co-selling e-book.

Tech ecosystem enablement tactics:

Adopt enablement tools. At Sharebite, a food benefits platform, Odedina included information about their integrations with tools like ADP and Workday and their use cases in the enablement curriculum. He also used Spekit, an enablement tool, to enable salespeople to hover over words or icons in Salesforce and other tools to learn more about them. 

By using a tool like Spekit, you can make it easier for your sales reps to reference information and resources about your integrations as they work. For example: If your SDR hovers over your tech partner Hextall & Co, they can learn about your joint value proposition and when to engage Hextall & Co. for support qualifying a prospect.

Establish a resources hub. Keep your sales team up to date on your partner’s software and features so they can provide prospects with relevant information. Agencies like Hero Digital and americaneagle.com have created internal resource hubs their sales team can reference to learn about their tech partners. Sendoso created a partner directory.  

Dedicate time during your enablement sessions to talk about top partners. SignEasy includes slides about their most strategic partnerships as part of their initial enablement training. They also implemented a buddy system so every new hire has ongoing support.

Image courtesy of SignEasy

Invite your partner to speak to your team. Provide your team with direct interaction with your partners to help them understand your joint value proposition and build trust with your partners. Freshworks brings their partners in to discuss their prospect accounts and generate warm intros same day. Invite your partners to “working sessions” to generate leads for each other, to your sales kickoff events to present, or even to your next team happy hour to get to know your team.

Tip #4: Develop Benchmarks, and Track Your Sales Team’s Ability to Hit Their Ramping Goals

Observe how participants in your enablement training are performing month over month, and compare their performance to sales reps who had no enablement training. A month or two after training, determine who among the enablement participants are hitting their ramping goals and who aren’t. 

Piece together trends that reveal why your cohort of sales hires have been successful or not. For example: You may have SDRs who are struggling to find the information they need in your knowledge base software. This could be an issue of: 

  • A gap in your enablement training
  • Too many hands in the pot. Perhaps your sales, marketing, and product marketing team are using too many different tech stack tools to store resources and/or they need guidance in how to organize the information in your knowledge base software 
  • Your sales rep not understanding the value of the resources in your knowledge base software or limiting themselves to a finite number of sales resources

“Do we need more effort? Or is it our effectiveness? It’s usually some mix of the two,” says Odedina.

Observe how your cohort of sales reps are performing overall (e.g. As an SDR team, they’re generating an average of five new prospects per day) and as individuals. Track individual performance by creating a stack rank. Consider creating a stack rank specific to your new hires that can evaluate their performance separately from your seasoned sales reps. Below are a couple of examples of stack rank models: 

Use the early metrics of average performance among your cohort and individual performance to set benchmarks. Then, compare the data month-over-month. 

Odedina suggests waiting a couple of months after launching your first enablement program to decide which metrics should be considered high or low. In the early days, track the correlation between specific metrics, like average number of dials in a day, to outcomes, like number of meetings. These analytics will help you finetune your enablement program to produce the results your sales team wants. 

“If we have a new hire and they do X, Y, and Z, they should produce this amount,” says Odedina.

Keep in mind: You are measuring the success of your cohort over the course of a 90-day time period and comparing their success to sales reps who did not participate in enablement or to their own success prior to enablement (for existing employees). Identify which numbers change based on particular training sessions you host, the new tools you adopt and onboard for your team, or the resources you create. Track changes like: 

  • The average deal closing in 30 days compared to 42 days in the previous quarter 
  • Improvements in closing rate 
  • An increase in sales conversations with less dials or emails required 

“[The enablement program] incrementally improved every month,” says Odedina. “It’s always going to evolve as things change with the product and with the industry.”

Olivia Ramirez 18 min

4 Tips for Launching a 30-60-90 Day Enablement Program for Your New Sales Hires

Teach your sales team how to identify your prospects' tech stacks, and use interactive quizzes to reinforce their learnings.

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