1. Tips and Tricks to Stay
Out of the Spam Folder
Presenters:
Elmer Thomas and Carly Brantz
Tuesday, May 29, 12
2. Carly Brantz
carly.brantz@sendgrid.com
@carlybrantz
Elmer Thomas
elmer.thomas@sendgrid.com
@thinkingserious
#SGWebinar
Tuesday, May 29, 12
Carly:
Hello
everyone,
I’d
like
to
welcome
everyone
today
to
our
webinar:
Tips
and
Tricks
to
Staying
out
the
Dreaded
Spam
folder.
My
name
is
Carly
Brantz
and
I
lead
the
inbound
markeHng
group
here
at
SendGrid
that
focuses
on
creaHng
content
and
educaHng
our
prospects
and
clients
about
email
delivery.
I’ll
be
joined
today
by
Elmer
Thomas
who
is
a
developer
evangelist.
Both
of
our
twiKer
handles
and
email
addresses
are
here
and
we
encourage
you
to
follow
up
with
us
with
any
quesHons
we
aren’t
able
to
get
to
during
today’s
presentaHon
3. Anybody there?
“If
your
emails
don’t
make
it
to
the
inbox,
you
are
talking
to
yourself.
Not
cool.”
-‐Email
Sending
Ninja,
Elmer
Thomas
#SGWebinar
Tuesday, May 29, 12
Carly:
You’re
all
here
today
because
landing
in
the
spam
folder
means
you
lose
out
on
your
opportunity
to
communicate
with
your
customers.
You
literally
as
Elmer
quote
reads
here
talk
to
yourself.
4. Email
Delivery
is
Never
Guaranteed
#SGWebinar
Tuesday, May 29, 12
Carly:
If
you
rely
on
email
to
communicate
with
your
customers,
then
you
need
to
know
about
one
of
biggest
issues
facing
app
developers
today
-‐
email
delivery
failures.
5. Updates Shipping Notifications
Confirmations
Account Verifications
TRANSACTIONAL
Alerts Receipts Statements
Notifications
Reminders Password Delivery
Cancellations
Announcements
#SGWebinar
Tuesday, May 29, 12
Carly:
This
means
that
the
transacHonal
email
you
send
like
email
confirmaHons,
shipping
noHces,
privacy
updates
and
friend
requests
being
deployed
though
your
systems
are
not
reaching
your
customers.
Consider
what
happens
if
your
email
doesn’t
arrive
in
the
inbox?
Your
customers
won’t
receive
their
purchase
confirmaHons
or
shipping
noHficaHons.
That
request
for
a
password
reset
never
arrives.
They’ll
never
know
that
someone
special
from
their
preferred
daHng
site
wants
to
meet
them.
6. 20% of Commercial
Email Never Arrives as Intended!
#SGWebinar
Tuesday, May 29, 12
Carly:
In
fact,
more
than
20%
of
commercial
email
never
reaches
the
inbox
resulHng
in
poor
customer
experiences,
loss
of
revenue
and
lack
of
trust
amongst
your
user
base.
7. How Email Appears to Work
Sender’s Outbox Recipient’s Inbox
#SGWebinar
Tuesday, May 29, 12
Carly:
Email
appears
to
be
fairly
cut
and
dry
right?
You
create
the
email,
push
send
and
the
recipient
of
your
email
receives
it.
8. How Email Actually Works
Sender’s Outbox Recipient’s Inbox
The Internet
Recipient’s Mail Server
Sender’s Mail Server (MTA) Anti-Spam Filter
(MTA)
#SGWebinar
Tuesday, May 29, 12
Carly:
In
reality,
email
delivery
is
a
much
more
complex
process.
The
fact
is
that
when
hit
“send”,
email
goes
through
all
sorts
of
check
and
balances
by
the
ISPs
and
spam
filters
to
prevent
malicious
email
from
infiltraHng
customer
inboxes.
Email
deliverability
is
a
science
with
proven
techniques
to
prevent
failures
and
improve
your
delivered
rates.
If
you
have
the
informaHon
and
tools
to
manage
it,
then
you
can
achieve
higher
return
on
your
email
markeHng
investment
in
the
long
run.
9. Spam
Filters
#SGWebinar
Tuesday, May 29, 12
Elmer:
Let’s
talk
about
how
SPAM
filters
work.
Understanding
what
stands
between
you
and
the
inbox
is
key.
Image
Source:
hKp://sendgrid.com/blog/10-‐Hps-‐to-‐keep-‐email-‐out-‐of-‐the-‐spam-‐folder
10. User
Interac9on
Tracking
Unread Mail
#SGWebinar
Tuesday, May 29, 12
Elmer:
Some
measure
and
track
user
interacHon
(messages
that
aren't
read,
or
aren't
opened
and
clicked
on,
are
more
likely
to
be
sent
to
the
Junk
folder)
11. Heuris9cs,
Sta9s9cs
&
Magic
#SGWebinar
Tuesday, May 29, 12
Elmer:
Some
use
heurisHcs
(rules,
oben
with
regular
expressions,
to
search
for
spammy
content),
message
structure
(does
this
look
like
a
NewsleKer
we've
seen
before?),
message
fingerprinHng
(look
up
fingerprint
to
see
if
it
matches
know
spam)
and/or
staHsHcal
methods
(Bayesian
filter:
Does
this
message
contain
words
similar
to
known
spam
or
known
clean
messages?)
12. User
Feedback
&
Community
Vo9ng
#SGWebinar
Tuesday, May 29, 12
Elmer:
Some
use
human
user
feedback
and
community
voHng
("This
is
spam"
buKon
in
mail
client
or
webmail
app.)
13. Reputa9on
#SGWebinar
Tuesday, May 29, 12
Elmer:
Some
look
at
sender
reputaHon
(based
on
sending
IP
or
domain)
14. There
is
No
Silver
Bullet!
#SGWebinar
Tuesday, May 29, 12
Elmer:
...but
there's
no
silver
bullet.
Spammers
adapt.
Filters
adapt.
Some
innocent
messages
get
caught
in
the
crossfire
(false
posiHves).
Image
Source:
hKp://sbrownehr.com
15. CAN-‐SPAM
Controlling
the
Assault
of
Non
-‐
Solicited
Pornography
And
MarkeHng
#SGWebinar
Tuesday, May 29, 12
Elmer:
Comply
with
CAN-‐SPAM
or
face
penalHes
up
to
$16,000
Reference:
www.bc.gov—bus61.shtm
16. CAN-‐SPAM
1.Don’t
Use
False
or
Misleading
Header
InformaHon
2.Don’t
Use
DecepHve
Subject
Lines
3.IdenHfy
the
Message
as
an
AdverHsement
4.Tell
Recipients
Where
You’re
Located
5.Tell
Recipients
How
To
Opt
Out
of
Receiving
Future
Email
From
You
6.Honor
opt-‐out
requests
promptly
7.Monitor
what
others
are
doing
on
your
behalf
#SGWebinar
Tuesday, May 29, 12
17. CAN-‐SPAM
TransacHonal
emails
are
exempt
from
CAN-‐SPAM
(Best
pracHce
is
to
comply
regardless)
#SGWebinar
Tuesday, May 29, 12
Elmer:
If
your
email
contains
only
transacHonal
emails
or
relaHonship
content,
then
you
are
exempt
from
these
rules;
however,
you
must
sHll
not
include
false
or
misleading
rouHng
informaHon.
18. Authen9cate
Your
Email
in
5
Easy
Steps
#SGWebinar
Tuesday, May 29, 12
Carly:
Email
authenHcaHon
has
a
proven
track
record
but
a
surprisingly
high
percentage
of
businesses
sHll
haven’t
implemented
it.
AuthenHcaHon
is
an
“ID
check”
for
your
mail
streams:
it
validates
that
the
email
is
actually
from
you
(and
not
some
spammer
impersonaHng
you).
AuthenHcaHng
your
mail
streams
does
not
ensure
your
email
will
be
delivered
but
it
helps
ISPs
to
further
differenHate
your
business
from
spammers
and
other
illegiHmate
senders.
AuthenHcaHng
your
email
is
one
posiHve
step
you
can
take
today
to
make
the
[email]
world
a
beKer
place.
While
it
seems
like
a
daunHng
task,
properly
implemenHng
authenHcaHon
can
significantly
improve
your
chances
of
reaching
the
inbox.
If
you’re
sending
transacHonal
email,
it’s
even
more
important
since
your
customers
are
expecHng
and
anHcipaHng
those
messages.
Let’s
get
started
on
the
basics
19. 1.
Audit
Your
Computer
#SGWebinar
Tuesday, May 29, 12
Carly:
As
a
first
step,
take
stock
of
all
systems
that
send
your
mail.
IdenHfy
all
machines
that
send
mail
for
your
company.
Next,
determine
the
IP
addresses
(if
you're
planning
to
use
SPF
or
SenderID)
and
sending
domains
used.
20. 2.
Create
Your
Authen9ca9on
Records
Sender
Policy
Framework
(SPF)
hKp://www.openspf.org
SenderID
hKp://www.microsob.com/senderid
Domain
Keys
IdenHfied
Mail
(DKIM)
hKp://www.dkim.org
#SGWebinar
Tuesday, May 29, 12
Carly:
Next
step
is
to
create
your
authenHcaHon
records.
There
are
three
accepted
methods
of
authenHcaHon:
Sender
Policy
Framework
(SPF),
SenderID
and
Domain
Keys
IdenHfied
Mail
(DKIM).
The
best
pracHce
is
to
implement
all
three
methods,
especially
if
you
have
high-‐volume
transacHonal
email
streams.
Get
details
on
the
various
types
of
authenHcaHon.
You
can
find
detailed
informaHon
on
the
following
websites:
DKIM:
hKp://www.dkim.org/
SenderID:
hKp://www.microsob.com/senderid
SPF:
hKp://www.openspf.org
21. 3.
Publish
Your
Authen9ca9on
Records
Via
Your
DNS
Records
Update
Your
DNS
Records
#SGWebinar
Tuesday, May 29, 12
Carly:
Step
3
is
to
publish
your
authenHcaHon
records.
If
you
are
using
SPF,
SenderID
or
DKIM,
work
with
whoever
manages
your
DNS
records
to
publish
the
email
authenHcaHon
records
you've
collected.
The
actual
publishing
is
easy;
finding
the
responsible
party
who
controls
your
DNS
may
be
the
tricky
part.
22. 4.
Setup
Your
Mail
Server
to
Sign
Outbound
Email
with
DKIM
#SGWebinar
Tuesday, May 29, 12
Carly:
Setup
your
mail
server
to
sign
outbound
email
with
DKIM.
DKIM
requires
that
your
MTA
have
the
appropriate
sobware
implementaHon
to
sign
all
outgoing
emails.
23. 5.
Test
by
Publishing
in
“Test”
Mode
#SGWebinar
Tuesday, May 29, 12
Carly:
Lastly,
you’ve
got
to
test
your
authenHcaHon
records.
SPF,
SenderID,
and
DKIM
provide
opHons
to
publish
your
records
in
“test”
mode.
This
provides
the
opportunity
for
tesHng
without
risking
delivery
failures.
24. Content
and
Relevancy
#SGWebinar
Tuesday, May 29, 12
Elmer:
Now
we
dive
into
the
actual
content
of
your
email.
I’ll
take
you
through
the
best
pracHces
to
ensure
that
your
messaging
is
structured
properly,
in
terms
of
the
email
content,
to
avoid
the
SPAM
filters.
25. Make
Unsubscribing
Easy
#SGWebinar
Tuesday, May 29, 12
Elmer:
Make
it
easy
to
unsubscribe
so
they
don't
hit
the
"This
is
SPAM"
buKon
26. Segment
Wisely
#SGWebinar
Tuesday, May 29, 12
Elmer:
Segment
by
demographics,
interests
and
purchase
behavior
to
increase
relevancy
and
value
27. Avoid
Phishing
Phrases
and
Trigger
Words
As
Seen
On F
r
e
e
Update
Your
Billing
InformaHon
Money
making
Please
Re-‐acHvate
Your
Account
Stock
Alert
Buy Click
Trigger Words Phishing Phrases
While
you
sleep
LifeHme Re-‐submit
Your
Payment
Info
Make
$
Miracle Update
your
payment
info
$$$
Beneficiary You
have
one
or
more
alerts
Get
paid
This
Isn’t
Junk
#SGWebinar
Tuesday, May 29, 12 F
r
r
e
e
F
e
e
Elmer:
100
SPAM
Trigger
Words
&
Phrases
to
Avoid:
hKp://blog.mannixmarkeHng.com/2009/08/spam-‐trigger-‐words/
Short
List
of
Common
Phishing
Phrases:
hKp://www.24hoursupport.com/index.php?opHon=com_content&task=view&id=192&Itemid=1
28. HTML
+
Text
#SGWebinar
Tuesday, May 29, 12
Elmer:
Include
a
text
version
if
sending
HTML
Emails
29. SPAM
Check
#SGWebinar
Tuesday, May 29, 12
Elmer:
Use
SPAM
checkers
before
sending
your
emails:
hKp://www.mailingcheck.com
hKp://spamassassin.apache.org
hKp://www.isnotspam.com
hKp://www.programmersheaven.com/webtools/Spam-‐Checker/spamchecker.aspx
30. Text:Image
Ra9o
#SGWebinar
Tuesday, May 29, 12
Elmer:
Maintain
a
good
text
to
image
raHo.
Don't
send
any
image-‐only
emails.
For
every
graphic
include
2
lines
of
text.
OpHmize
your
images.
31. Too
Big
#SGWebinar
Tuesday, May 29, 12
Elmer:
Avoid
Large
AKachments
and
certain
aKachment
types.
In
general,
.jpg,
.gif,
.png
and
.pdf
aKachments
are
safe
to
send,
provided
you
include
some
content
in
the
email
as
well.
Executable
aKachments
such
as
.exe,
.zip,
.swf,
etc.
should
be
avoided
enHrely.
Generally,
you
should
not
send
aKachments
to
people
on
your
list
that
are
not
expecHng
them.
If
you
need
to
email
a
large
aKachment
or
an
aKachment
type
that
usually
can
be
flagged
as
spam
or
trigger
virus
scanners,
we
recommend
a
service
such
as
DropBox.com.
If
the
aKachment
contains
sensiHve
data,
you
may
consider
using
your
company’s
secure
FTP
server.
Image
Source:
hKp://journal.zenyee.com
32. HTML,
CSS,
and
Images
#SGWebinar
Tuesday, May 29, 12
Elmer:
Use
the
ALT
tag
&
store
images
on
a
web
server.
Don't
use
CSS.
Double
check
your
message's
HTML
content
code:
validator.w3.org
33. Permission
Marke9ng
Right
Message
to
the
Right
Person
at
the
Right
Time
with
the
Right
Frequency
#SGWebinar
Tuesday, May 29, 12
Elmer:
Permission
MarkeHng:
hKp://sethgodin.typepad.com/seths_blog/2008/01/permission-‐mark.html
Ask
to
be
on
their
white
list.
Most
of
the
Hme,
when
someone
marks
your
message
as
spam,
It
wasn't
the
right
message
(relevance)
Or
it
wasn't
sent
to
the
right
person
(confirmed
opt-‐in
list
or
purchased
list
or
stale
list?)
Or
it
wasn't
sent
at
the
right
Hme
(obtained
the
email
address
years
ago
while
working
for
a
different
company
selling
a
different
product)
Or
it
wasn't
sent
with
the
right
frequency
(recipients
get
"email
faHgue"
if
you
send
too
oben
(use
a
preference
center),
or
may
forget
about
you
if
you
don't
send
oben
enough.)
34. Why SendGrid?
We make email delivery simple and easy for developers
everywhere.
#SGWebinar
Tuesday, May 29, 12
Carly:
As
we
wrap
up
today,
I
wanted
to
quickly
review
SendGrid’s
offering.
We
provide
a
cloud-‐based
service
that
replaces
your
company’s
email
infrastructure
and
provides
everything
you
need
to
operate
a
reliable
and
scalable
outbound
email
delivery
system.
Based
on
the
fact
that
you
have
aKended
this
webinar,
I
think
you
all
understand
how
crucial
email
delivery
is
to
your
success.
SendGrid
helps
you
focus
on
your
business
without
the
cost
and
complexity
of
owning
and
maintaining
an
email
infrastructure.
Our
technology,
advanced
analyHcs,
and
flexible
APIs
are
designed
for
all
types
of
email
—
from
transacHonal
messages
generated
by
an
applicaHon,
to
direct
markeHng
campaigns.
35. What Our Clients Are Saying
“Marrying the SendGrid Platform with SoftLayer's offering in both Infrastructure as a
Service and Cloud Computing really does give the customers the most robust, turnkey
offering available to the market today.”
“Their account management team is responsive and proactive, providing us with the
space we need to focus on strategic plans, rather than day to day email management.”
“We’re now enjoying email delivery rates of 96% and have saved thousands of dollars
in engineering resources.”
#SGWebinar
Tuesday, May 29, 12
Carly:
Here
is
a
sampling
of
the
types
of
companies
that
work
with
SendGrid
and
what
they
are
saying
about
SendGrid
and
their
improved
email
performance.
36. Key Takeaways
#SGWebinar
Tuesday, May 29, 12
Elmer:
Build
and
Maintain
Your
ReputaHon
Check
All
of
the
Technical
Checkboxes
Be
Relevant
37. Learn More
• Upcoming Webinar:
- “How to Get The Most out of Transactional Email”
• SendGrid’s Deliverability Guide
• SendGrid’s Blog
- www.sendgrid.com/blog
#SGWebinar
Tuesday, May 29, 12
Carly:
Our
plan
moving
forward
is
to
host
these
kinds
of
webinars
monthly
and
I
want
to
encourage
you
to
sign
up
for
our
next
webinar
where
we
will
cover
TransacHonal
Email.
You
can
sign
up
directly
from
our
homepage.
In
addiHon,
we
have
a
wealth
of
informaHon
on
our
blog.
You
can
sign
up
and
stay
on
top
of
email
trends,
get
guidance
on
APIs,
learn
about
our
latest
partnerships
and
find
out
the
latest
informaHon
about
SendGrid.
You
can
sign
up
at
sendgrid.com/blog.
