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The Best Sales Strategy Content Online: From Expert Advice to Building the Ultimate Sales Team
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The Best Sales Strategy Content Online: From Expert Advice to Building the Ultimate Sales Team

The Best Sales Strategy Content Online: From Expert Advice to Building the Ultimate Sales Team

August 1, 2021
13 Jogs
Why it matters?

Is your sales funnel just not converting? Are you looking for a new sales job but need to set yourself apart from the competition? If so, then this blog post is for you. We outline the best content available online on how to build a winning sales strategy that meets the needs of any business and provides advice on how to optimize your process in order make more money. This includes content about building an effective team of professionals who are willing and able to generate leads for your company as well as execute those leads when they come in. Not only will these strategies help you get ahead of competitors, but they will also help grow revenue by maximizing conversion rates.

"What's the best way to get sales?" This is a question we often hear from professionals looking to improve their skills in sales. Whether you are an existing sales executive looking to improve your skills or performance, or someone who wants to get into the industry, there are too many resources available for you, too little time to consume it all, and it can be difficult knowing where to begin when searching for these resources online. We have compiled the essential list of content for to save you time so you can focus on generating more revenue for your company. Enjoy!

The Content

Each link contains a summary produced by one of Joggo's geniuses so you can decide where to spend your time learning more

March 12, 2019
Pete Prowitt

5 lessons learned starting a new team within our sales organization

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The Summary

Relentlessly Measure Impact

  • Make sure the time and effort required to achieve your goals are worth it.
    • Requires seeing a big enough impact on customer expansion to justify the cost for additional headcount.

Have a Bias Toward "Yes"

  • Comedians make "yes, and" statements to help them take a concept and build on it in creative ways.
  • Similarly, starting a new sales team requires taking a hypothesis and constantly evolving it.
    • Change your hypothesis as info. emerges.
    • Lean toward "yes, and" statements.

Hire for Ownership

Hire relationship managers who think and operate like business owners.

Channel Your Inner MacGyver

You'll need to be extremely resourceful when starting a new sales team because they usually operate without the same level of cross-functional support that established teams enjoy.

Find Your Village and Cultivate It

Seek out and invest in fostering a positive relationship with your teammates because you will need their help in the future.

Courtney Chuang

8 steps to create your winning sales strategy, according to industry leaders

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The Summary

Understand what it takes to attract your target customer based on 3 key sales models.

  1. Enterprise
    1. Attain high-value customers through a complex sales process.
    2. e.g. HubSpot
  2. Transactional
    1. Attain high-value customers through a simple sales process (self-service).
    2. e.g. Amazon
  3. Self-service
    1. Attain low-value customers through a simple sales process.
    2. e.g. Xero

Know when to add sales to a self-serve business model.

  • If you're selling something with a low average contract value (e.g. $1000 for the year), sales are not critical.
  • If you're selling something with a high average contract value (e.g. above $5,000-$10,000), sales are critical.

Establish clear, differentiated roles on your sales team.

e.g. Inbound and outbound sales teams require vastly different skills and workflow.

Define your ideal customer profile (ICP).

  • Good ICPs should:
    • Enable you to identify a good prospect quickly
    • Enable you to simply convey the ICP to someone else in such a way that they can find other ICPs.
    • Be defined so systems can be built to identify them.
  • e.g. Heads of sales with teams larger than 50 people in tech.

Act as a consultant to your prospects.

  1. Engage with prospects in their context.
  2. Understand the specific challenges they're trying to solve.
  3. Translate the generic marketing strategy on your website to their business.
  4. Tell the story from their perspective.
  5. Follow up

Be deliberate when moving upmarket.

Maintaining a simple sales process while introducing more complex products and purchase processes requires careful planning and execution.

Experiment with your sales strategy before you pivot.

  1. Generate Hypothesis
    1. What sales strategy are you testing?
  2. Design Experiment
    1. Agree to a timeline and define goals.
  3. Run Experiment
    1. Track metrics and KPIs
  4. Analyze Results
    1. If it works, how far can it scale?

Use resellers and channel partners to accelerate growth.

Only do so when you're 6 months to 1 year in, have a product that has traction and growth, and have found success with content marketing.

Alan Gleeson

9 essential sales steps you need to grow your SaaS startup

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The Summary

Selling B2B software can be challenging, especially in the early days when it can be difficult to generate leads as resources are tight, and sales experience is low. Here is a simple sales methodology to help early stage SaaS businesses guide themselves.

9 Essential Sales Steps to Grow your SaaS Startup

  1. Define your marketing personas
    1. Create marketing personas that represent your ideal prospect or your ideal customer profile and search for your network for representatives of these profiles
  2. Meet your target users and get feedback
    1. The purpose of these meetings is to gain a deep understanding of the problem you believe you can solve for them.
    2. Listen to how they describe how they currently undertake the tasks that your solution is designed to help
  3. Iterate the product based on feedback
    1. Use these initial interactions to gain insights that will help product development
  4. Identify a market specific methodology
    1. Some basic training can ensure that you are equipped to engage with prospects in confidence
    2. Awareness of sales methodologies does ensure your approach is both scientific and rigorous
  5. Put a well-defined sales process in place
    1. Define what the various stages in your pipeline are, and how to move a prospect along the pipeline
  6. Create compelling content to help generate leads
    1. Gate the most valuable content behind a form where prospects provide information about themselves in return for access
  7. Qualify your prospects
    1. Utilize marketing automation software to send emails over a period of time that offer value, ensuring you stay at the forefront of their mind
    2. Consider using chat bots as an alternative to forms
  8. Managing the first sales meeting
    1. Don’t default to presentation mode; instead, you need to view the interaction as an information exchange where you are looking to surface their needs.
  9. Close the deal
    1. If your solution addresses their needs, you can then showcase the power of your product before asking for the business
First Round Review

Designing Your Sales Stack so that Customers Come to You  

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The Summary

Most companies rely on outbound sales (prospecting and outreach) to generate revenue and close deals. It is important to turn your outbound sales into inbound opportunities.

Understanding Inbound

This is traffic that's driven to a site organically or via marketing campaigns such as advertising, social media, content etc. The process of creating an online advertisement involves: - Choosing the goal or objective of your campaign - Choosing your target audience - Finding the right image, description, call to action that your targets can relate to This method is ineffective because it can be very expensive and might be great for getting views on your website, but not as much for conversions or engaging people in a buying process. 

How to Turn Your Outbound Marketing Into Inbound Opportunities

  • Figure out your target audience or Ideal Customer Profile
    • The better you can target and more granular you can get with your customer profile, the more successful your outbound campaigns will be.
    • You can target by a recent event - not just by static attributes like location and age range.
  • Get the right contact Info
  • Research, messaging and call to action
    • Find out as much information as possible on the company and individual contacts before you reach out to important prospects.
  • Ensure the message delivery is accurate and optimize as you go.
David Frankel
Founder Collective

Startups should read this checklist before they go “whale hunting” for big partners

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The Summary

Many promising startups have blown up due to ill-advised business development deals that swelled teams in a bout of euphoria only to see them wither if interest and focus from their partner wanes. Ask yourself these questions before going whale hunting:

How much monthly recurring revenue will it add to your business?

Once that money is spent, what will the ongoing revenue be? What is the opportunity cost of not supporting the current business plan? 

How will this project help your core business?

If the project will allow the startup to speed up the development of a core technology that is generally applicable to other customers, it would seem far more worthy of consideration.

What happens if this doesn’t work out?

When considering a high-risk, high-reward partnership, founders need to spend time envisioning a gruesome demise.

How well do you understand the bigger company?

Founders with little exposure to big companies are susceptible to misreading cues. 

Are you aware of the work pace differential?

Startups often drown in the number of process leviathans required to make the smallest of improvements while this is not the case for big companies.

Who are the internal champions?

Promising projects can die on the vine because the internal champion gets reassigned or leaves the company. Successful partnerships will involve multiple high-level people from the larger organization. 

Is the project a priority for the Chief Experience Officer/Vice President?

Below the level of a VP or CXO-level executive, we’ve seen startups spend large sums and risk their future on what amounts to a proof of concept project for a mid-level director with no real juice.

Are you competing with another startup?

Founders considering competing with another startup should give serious thought to skipping the process and building out a less concentrated revenue base with fewer impediments while your competitors fight to the death.

Pete Prowitt

The Agile Arrow – a visual framework for managing complex sales deals

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The Summary

  • Closing complex deals is more than just selling
  • Use project management skillset to prioritize people, work, and outcomes

Complex deals, complex problems

  • Complex deals require high level visibility
  • Easy to lose track of objectives without a framework

Agile Principles

  1. Simplicity
  2. Add changing requirements
  3. Build a deal around motivated individuals

Visualize the Arrow

  • Create an arrow with different milestones 
  • Each milestone can have goals tied to it

Putting faces to the Arrow

  • For each milestone add the most important stakeholders
  • Helps focus on only what is relevant to that group
  • Adapt, present in simplest way possible, and focus on stakeholders
October 12, 2017
Sean Siddhu

Why SaaS sales people should think like consultants

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The Summary

Best Practice 1 - Understand Your Prospect's Business

  • Understand their business so that you can understand other uses for the product
  • Upcoming business needs will provide you with support that your product should be their long-term solution

Best Practice 2 - Don't Oversell

  • Suggestions shouldn't be one-size-fits-all but align to customer needs
  • Do not impose a higher-cost solution on a prospect if it does not fit their needs to build trust

Best Practice 3 - Use Product Weakness to Underscore Product Strength

  • Pointing out a product's weakness allows you to see if a customer is a good fit and builds trust with the customer
  • Be as eager to disqualify a prospect as you are to qualify Key Takeaway: aim for the value proposition of your product as it relates to your customer and the money will follow
October 24, 2017
Andy Raskin

The Greatest Sales Pitch I’ve Seen All Year

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The Summary

Drift's CEO has transformed the company into a movement using a compelling strategic story with 5 parts:

Start with a big, undeniable change that creates stakes

  • Your most formidable obstacle is prospects' adherence to the status quo
    • Drift addresses change that is undeniably happening independently of Drift, which gives rise to high stakes

Name the enemy

  • Naming your customer's enemy differentiates you in relation to the old world your competitors represent
    • Drift invites you to join them in a revolution & fight a common foe

Tease the "Promised Land"

  • The "Promised Land" should be both desirable & difficult for prospects to reach without you
    • Drift plants a question in audiences' minds: "OK, so how do I win?"

Position capabilities as "magic" for slaying "monsters"

  • Once audiences buy into your Promised Land, impress them with your capabilities & product

Present your best evidence

  • Audiences will still be skeptical, so show evidence of your ability to deliver
  • The best evidence is stories about people who say you helped them reach the Promised Land

The Rise of Story-Led Differentiation

  • Product differentiation has become indefensible. Competitors can copy your features virtually instantly.
  • The only thing they can't replicate is trust that customers feel for you & your team.

Drift's Story Works Because They Tell It Everywhere... & Commit To Making It Come True

Peter Kazanjy
First Round Review

Building Your Best Sales Deck Starts Here  

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The Summary

Key success metric of salespeople is being able to shift between credibility of the product without agonizing over the details. Using a Powerpoint to support your conversations is the best tool.

A sales deck should include answers to the following?

  1. What is the problem you’re solving?
  2. Who has it?
  3. What are the associated costs of the problem?
  4. What are the existing solutions and their shortfalls?
  5. What has changed to enable a new solution?
  6. How does it work?
  7. What is the qualitative/quantitative proof that yours is a superior solution?
  8. How much does it cost?

Don’t forget!

  • Additional “sub-chapter” slides can be included on aspects of your value prop as noted by the questions above.
  • Think of these are 1a, 1b, 1c, etc. slides.
  • Focus on the MVP deck first and add additional flair later.
  • Have one master slide deck and create other versions depending on your audience.

Pointers for Sections of the Sales Narrative

  • Problem and Who Has It
    • Start here so you can tell if your audience actually has the problem; include data to validate the problem
  • Cost of the Problem
    • Use data to show how much the problem is costing the company; rely on metrics to help prove your point
  • Existing Solutions and Their Challenges
    • Bit of a tightrope; use this section to level set audience with market leaders / standards if they exist and how your solution overcomes gaps
  • What’s Changed
    • This can help assess the audiences understanding and allow you to explain what has changed in the market and how it impacts your audience
  • How Your Solution Works
    • Use a visualization to explain your product simply; can show your product on its own or how it works in comparison to market standards
  • Quantitative / Qualitative Proof of a Better Solution
    • Use metrics and numbers to explain why you and why now; can also use customer reviews and company awards and press as evidence of product superiority
  • Pricing
    • Include base price and variations as relevant
  • Appendix
    • Use for information that isn’t core but important to some customers
      • (i.e., integrations with other programs, competitor analysis);
      • Rule of thumb is to add an appendix slide the second time a question is asked Create a deck for presenting and then follow up with a standalone deck. These are typically different in content.
June 28, 2018
Steli Efti

Don’t forget the service in SaaS: how your sales team can provide world-class service

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The Summary

Your People are as Important as Your Product

  • Startups need to focus on providing more service for customers especially in sales, support and success.
  • This is especially true in B2B where the buying process is more complicated and implementation costs are higher.
  • Self-serve software isn't responsible for enterprise-level customers as there is more need for training, onboarding, etc.

Self-Serve Pros

  • Scales easier
  • Prospects can make their own decision and take control of their success
  • Incur less costs and drive down product price
  • Highly technical users prefer self-serve

Self-Serve Cons

  • Fall out of touch with customers and lose customer insights
  • Lose ability to build brand in a crowded market
  • Can easily lose human element of your product which differentiates you

3 Simple Ways to Provide Great Service

  1. Send all communication from a personal email address
  2. Spend time with your prospects and customers
  3. Share support responsibilities across sales and customer service
October 1, 2019
Elad Gil
Elad Gil

Fear of Sales

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The Summary

Why do product-center founders fear sales? 1) Familiarity Even though founders like to have familiarity with their own sales, they have to learn how to hire a sales leader just like how they also have a finance and PR team. 2) Perception of viewing sale applicants as liberal art degrees who were athletes in college Sales productivity is really easy to track, so founders shouldn’t fear the stereotypical profile of sales managers and they should just hire them and check on them. 3) Cultural concerns It’s certain that sales will change the culture, so instead of fighting it, founders should learn how they can productively incorporate sales people. 4) The fear of overspend and crash & burn If a company hires a lot of sales people before it has a successful sales model, the company may lose a lot of money. Thus, it is often better to start sales teams small and experimental before enlarging the team.

December 3, 2020
Sarah Wang, David George

The “$20M to $500M” Question: Adding Top Down Sales

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The Summary

For many enterprise startups, the dominant initial go to market (GTM) strategy has been growth and sales. However, a bottom up GTM is not enough to unlock the full potential of a market. The introduction of top down sales is one of the most important inflection points in many enterprise companies.  

Do you even need top down sales to scale?

  1. Initial growth is often the result of the product 
  2. As products proliferate through enterprise customers, there's a limit to users who will discover it or pay for it on their own 
  3. Yet, enterprise-wide deployment creates new users and use cases 

When should you add top down sales?

  1. The bottom up flywheel is working 
    1. Achieving between $20M to $30M ARR in bottom up-driven sales is a strong leading signal 
    2. Certain penetration statistics can also be a leading indicator 
    3. The bottom up motion serves as an important pipeline generator for the most successful top down sales 
  2. The business is demanding a top down solution 
    1. Critical to remember that individuals don’t buy enterprise features, businesses buy them. 

First leadership hire and rep compensation

  1. First leadership hire must be a: 
    1. Collaborative decision maker 
    2. Analytical and technical orientation 
    3. Long term relationship building 
    4. Enterprise sales experience 

How do you compensate your team?

  1. Align their team’s activities with the goals of the business  
  2. Tie these plans to the work that the individual sales rep is actually in control of 
  3. Incentivize the team to ensure that both the initial landing and net expansion are successful

How do you reconcile top down with bottom up pricing?

  1. Hybrid model: Full transparency for smaller self-serve customers, paired with the ability to negotiate custom enterprise pricing 
    1. Products with competitive environments 
    2. Majority of sales leaders believed a hybrid pricing model inclusive of discounting worked best for their companies 
  2. Self serve applied to enterprise sales: This approach entails full pricing transparency and a zero exceptions approach to discounting 
    1. Works for companies with limited competitions and newer use cases 

When do you start focusing on customer retention?

  1. Nearly all sales leaders we spoke with wished they had focused on retention sooner. 
  2. It should be built up alongside the sales effort 
  3. As the company scales, the role of customer success will evolve 

Looking ahead

  1. There is no right way to scale top down GTM operations 
  2. A truly successful go to market transformation requires product marketing, customer success, and product infrastructure also
April 13, 2018
Steli Efti

The 5 insights understood by all great SaaS sales reps

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The Summary

Great SaaS sales reps (efficient, motivated, effective & reactive) can change your entire business.

What is SaaS sales?

Selling web-based software to clients, focusing on acquiring new customers & upselling/retaining current clients.

Top 5 SaaS sales tips

  1. Upsell value to existing customers
    1. Integrate the product into your efforts to re-engage. Pay attention to reasons for the customer to upgrade.
  2. Persistence
    1. Once you get through to the prospect, you deliver value that will drive meaningful results
  3. Use technology
    1. Modern CRM tools & social media constantly create new ways for users to interact
  4. Marketing metrics influence sales metrics
    1. The best sales reps recognize the role of marketers. Sales reps can provide the marketing team insights.
  5. A growing sales team creates a growing company
    1. Sales reps need to view their colleagues as partners, not competitors

Become a better SaaS sales rep

Be committed to learning. Invest in yourself & ensure that you're working at an organization that is willing to invest in you